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Structure of 262450-65-7

Chemical Structure| 262450-65-7

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Product Details of [ 262450-65-7 ]

CAS No. :262450-65-7
Formula : C8H7BrO2
M.W : 215.04
SMILES Code : O=CC1=CC(OC)=CC(Br)=C1
MDL No. :MFCD06797975
InChI Key :GCXBEEKTPWZHJN-UHFFFAOYSA-N
Pubchem ID :10608698

Safety of [ 262450-65-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 262450-65-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 46.02
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

26.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.97
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.83
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.27
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.86
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.65
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.32

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.23
Solubility 0.127 mg/ml ; 0.000592 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.04
Solubility 0.196 mg/ml ; 0.000912 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.33
Solubility 0.0999 mg/ml ; 0.000465 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.6 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.54

Application In Synthesis of [ 262450-65-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 262450-65-7 ]

[ 262450-65-7 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 75-52-5 ]
  • [ 262450-65-7 ]
  • 2-(3-bromo-5-methoxyphenyl)nitroethylene [ No CAS ]
  • 2
  • [ 262450-64-6 ]
  • [ 262450-65-7 ]
  • 3
  • phenylmagnesium bromide [ No CAS ]
  • [ 262450-65-7 ]
  • [ 1026043-63-9 ]
  • 4
  • [ 109-77-3 ]
  • [ 99-07-0 ]
  • [ 262450-65-7 ]
  • 2-Amino-3-cyano-7-dimethylamino-4-(3-bromo-5-methoxyphenyl)-4H-chromene [ No CAS ]
  • 5
  • [ 262450-65-7 ]
  • [ 1026981-89-4 ]
  • 6
  • [ 262450-65-7 ]
  • 4-(3-benzyl-5-methoxy-phenyl)-2,4-dioxo-butyric acid methyl ester [ No CAS ]
  • 7
  • [ 262450-65-7 ]
  • 4-(5-Benzyl-3-methoxyphenyl)-2,4-dioxobutyric acid [ No CAS ]
  • 8
  • [ 29578-83-4 ]
  • [ 262450-65-7 ]
  • 9
  • [ 157893-14-6 ]
  • [ 262450-65-7 ]
  • 10
  • [ 262450-65-7 ]
  • [ 262450-67-9 ]
  • 11
  • [ 262450-65-7 ]
  • 2-(6-bromo-8-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-phenol [ No CAS ]
  • 12
  • [ 262450-65-7 ]
  • 2-(8-bromo-6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-phenol [ No CAS ]
  • 13
  • [ 262450-65-7 ]
  • 2-(8-bromo-2-ethyl-6-methoxy-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-phenol [ No CAS ]
  • 14
  • [ 262450-65-7 ]
  • 2-(6-bromo-2-ethyl-8-methoxy-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-phenol [ No CAS ]
  • 15
  • [ 262450-65-7 ]
  • 8-bromo-1-(2-hydroxybenzyl)-6-methoxy-2-propyl-1,2,3,4-tetrahydroisoquinoline [ No CAS ]
  • 16
  • [ 262450-65-7 ]
  • [ 262450-76-0 ]
  • 17
  • [ 262450-65-7 ]
  • [ 262450-69-1 ]
  • 18
  • [ 262450-65-7 ]
  • [ 262450-70-4 ]
  • 19
  • [ 262450-65-7 ]
  • [ 262450-71-5 ]
  • 20
  • [ 262450-65-7 ]
  • [ 262450-77-1 ]
  • 21
  • [ 262450-65-7 ]
  • [ 262450-78-2 ]
  • 22
  • [ 68-12-2 ]
  • [ 262450-65-7 ]
YieldReaction ConditionsOperation in experiment
98% n-BuLi (2.6 mL of a 1.6 M solution, 1.1 equiv) was added slowly to a solution of 46a (1.0 g, 3.8 mmol) in Et2O (20 mL) cooled to -78 C. under an N2 atmosphere. The solution was stirred for 45 min and DMF was added via syringe. The solution was warmed slowly to RT, added to saturated NH4Cl, and extracted with ether. The organic phase was washed with brine and dried (MgSO4), filtered and evaporated to afford 0.80 g (98%) of 46b.
98% n-BuLi (2.6 mL of a 1.6 M solution, 1.1 equiv) was added slowly to a solution of the R-21a (1.0 g, 3.8 mmol, CAS Reg. No. 74137-36-3) in Et2O (20 mL) cooled to -78 C. under an N2 atmosphere. The solution was stirred for 45 min, and DMF was added via syringe. The solution was warmed slowly to RT, added to saturated NH4Cl, and extracted with ether. The organic phase was washed with brine and dried (MgSO4), filtered and evaporated to afford 0.80 g (98%) of R-21b.
step 2-To a solution of 50b (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -780 C for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (3 to 5% EtOAc) to afford 51
To a solution of R-27b (60 g, 0.2256 mol) and anhydrous Et2O (I L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (3 to 5% EtOAc) to afford R-28.

  • 23
  • [ 262450-65-7 ]
  • [ 867366-90-3 ]
YieldReaction ConditionsOperation in experiment
97% With hydroxylamine hydrochloride; In pyridine; ethanol; at 65℃; for 16h; A solution of the aldehyde 180b (12.0 g, 56 mmol), hydroxylamine hydrochloride (19.4 g, 5 equiv), EtOH (100 mL) and pyridine (10 mL) was heated to 65 C. for 16 h. The mixture was cooled to RT, and partitioned between 50% EtOAc/hexanes and water. The organic layer was washed with brine and dried (MgSO4). The volatile materials were evaporated to afford 12.4 g (97%) of the oxime. This material was dissolved in anhydrous dioxane (100 mL) and pyridine (26 mL, 6 equiv). The solution was cooled to 0 C., TFAA (15 mL, 2 equiv) was added, and the mixture was allowed to warm to RT. The solution was stirred for 2 d, and warmed to 60 C for 1 h. The mixture was cooled to RT, and added carefully to ice water. The mixture was extracted with methylene chloride, and the combined organic layers were washed with water, 1 M HCl, and brine. The organic layer was dried (MgSO4) and evaporated to afford 10.4 g (90%) of 180c,
97% With pyridine; hydroxylamine hydrochloride; In ethanol; at 65℃; for 16h; A solution of the aldehyde 46b (12.0 g, 56 mmol), hydroxylamine hydrochloride (19.4 g, 5 equiv), EtOH (100 mL) and pyridine (10 mL) was heated to 65 C. for 16 h. The mixture was cooled to RT, and partitioned between 50% EtOAc/hexanes and water. The organic layer was washed with brine and dried (MgSO4), filtered and the volatile materials were evaporated to afford 12.4 g (97%) of the oxime. This material was dissolved in anhydrous dioxane (100 mL) and pyridine (26 mL, 6 equiv). The solution was cooled to 0 C., TFAA (15 mL, 2 equiv) was added, and the mixture was allowed to warm to RT. The solution was stirred for 2 d, and warmed to 60 C. for 1 h. The mixture was cooled to RT, and added carefully to ice water. The mixture was extracted with DCM, and the combined organic layers were washed with water, 1 M HCl, and brine. The organic layer was dried (MgSO4) and evaporated to afford 10.4 g (90%) of 46c,
97% With pyridine; hydroxylamine hydrochloride; In ethanol; at 65℃; for 16h; A solution of the aldehyde R-21b (12.0 g, 56 mmol), NH2OH.HCl (19.4 g, 5 equiv), EtOH (100 mL) and pyridine (10 mL) was heated to 65 C. for 16 h. The mixture was cooled to RT, and partitioned between 50% EtOAc/hexanes and water. The organic layer was washed with brine and dried (MgSO4). The volatile materials were evaporated to afford 12.4 g (97%) of the. oxime. This material was dissolved in anhydrous dioxane (100 mL) and pyridine (26 mL, 6 equiv). The solution was cooled to 0 C., TFAA (15 mL, 2 equiv) was added, and the mixture was allowed to warm to RT. The solution was stirred for 2 d, and warmed to 60 C for 1 h. The mixture was cooled to RT and added carefully to ice water. The mixture was extracted with DCM, and the combined organic layers were washed with water, 1 M HCl, and brine. The organic layer was dried (MgSO4) and evaporated to afford 10.4 g (90%) of R-21c.
97% With pyridine; hydroxylamine hydrochloride; In ethanol; at 65℃; for 16h; step 2-A solution of 1-bromo-3-formyl-benzaldehyde (12.0 g, 56 mmol), hydroxylamine hydrochloride (19.4 g, 5 equiv), EtOH (100 mL) and pyridine (10 mL) was heated to 65 C. for 16 h. The mixture was cooled to RT, and partitioned between 50% EtOAc/hexanes and water. The organic layer was washed with brine and dried (MgSO4). The volatile materials were evaporated to afford 12.4 g (97%) of the oxime.
97% With pyridine; hydroxylamine hydrochloride; In ethanol; at 65℃; for 16h; A solution of 1-bromo-3-formyl-benzaldehyde (12.0 g, 56 mmol), hydroxylamine hydrochloride (19.4 g, 5 equiv), EtOH (100 mL) and pyridine (10 mL) was heated to 65 C. for 16 h. The mixture was cooled to RT, and partitioned between 50% EtOAc/hexanes and water. The organic layer was washed with brine and dried (MgSO4). The volatile materials were evaporated to afford 12.4 g (97%) of the oxime. This material was dissolved in anhydrous dioxane (100 mL) and pyridine (26 mL, 6 equiv). The solution was cooled to 0 C., TFAA (15 mL, 2 equiv) was added, and the mixture was allowed to warm to RT. The solution was stirred for 2 d, and warmed to 60 C for 1 h. The mixture was cooled to RT, and added carefully to ice water. The mixture was extracted with DCM, and the combined organic layers were washed with water, 1 M HCl, and brine. The organic layer was dried (MgSO4) and evaporated to afford 10.4 g (90%) of 3-bromo-5-methoxy-benzonitrile.
97% With pyridine; hydroxylamine hydrochloride; In ethanol; at 65℃; for 16h; step 2-A solution of the aldehyde R-21b (12.0 g, 56 mmol), hydroxylamine hydrochloride (19.4 g, 5 equiv), EtOH (100 mL) and pyridine (10 mL) was heated to 65 C. for 16 h. The mixture was cooled to RT, and partitioned between 50% EtOAc/hexanes and water. The organic layer was washed with brine and dried (MgSO4). The volatile materials were evaporated to afford 12.4 g (97%) of the oxime. This material was dissolved in anhydrous dioxane (100 mL) and pyridine (26 mL, 6 equiv). The solution was cooled to 0 C., TFAA (15 mL, 2 equiv) was added, and the mixture was allowed to warm to RT. The solution was stirred for 2 d, and warmed to 60 C for 1 h. The mixture was cooled to RT, and added carefully to ice water. The mixture was extracted with DCM, and the combined organic layers were washed with water, 1 M HCl, and brine. The organic layer was dried (MgSO4) and evaporated to afford 10.4 g (90%) of R-21c,
With pyridine; hydroxylamine hydrochloride; In ethanol; at 65℃; for 16h; A solution of <strong>[262450-65-7]3-bromo-5-methoxybenzaldehyde</strong> (4.02 g, 18.7 mmol) and hydroxylamine hydrochloride (6.50 g, 93.5 mmol) in pyridine (50 mL) and EtOH (50 mL) was heated to 65 C. for 16 h. The solvent was removed, and the remaining materials were partitioned between 1:1 EtOAc/hexanes (150 mL) and H2O (75 mL). The organic layer was washed with brine (60 mL), and the solvents were evaporated. The remaining oil was dissolved in anhydrous dioxane (50 mL), and trifluoroacetic anhydride (5.1 mL, 37.4 mmol) and pyridine (9.07 mL, 112.2 mmol) were added. The mixture was heated to 60 C. for 3 h and then cooled to RT. CHCl3 (100 mL) was added, and the organic layer was washed with H2O (2×50 mL), 5% aqueous HCl solution (30 mL), brine (30 mL), and dried with anhydrous MgSO4. The solvents were removed to provide a white solid. This solid was placed in a 150 mL flask that was flushed with nitrogen. Collidine (40 mL) and LiI (7.92 g, 59.10 mmol) were added, and the mixture was heated to 180 C. for 5 h. The reaction mixture was cooled to RT, and partitioned between H2O (400 mL) and EtOAc (100 mL). The layers were separated, and the aqueous layer was acidified with 10% aqueous HCl solution, and extracted with 2:1 EtOAc/hexanes (3×125 mL). The combined organic layers were washed with H2O (100 mL), 10% aqueous HCl solution (2×50 mL), brine (75 mL), and dried with anhydrous MgSO4. The solvents were evaporated and the resulting solid was purified by flash chromatography on silica gel (10% to 40% EtOAc/hexanes) to provide 3.40 g (92%) of 3-bromo-5-hydroxybenzonitrile (116).

  • 24
  • [ 262450-65-7 ]
  • [ 199177-26-9 ]
YieldReaction ConditionsOperation in experiment
With boron tribromide; In dichloromethane; at -78 - 20℃; for 2h; A solution of BBr3 (29.1 mL of a 1.0 M solution in DCM, 29.1 mmol) was added slowly to a solution of 170a (2.5 g, 11.62 mmol) in anhydrous DCM (25 mL) maintained under N2 at -78 C. The orange solution was warmed to RT, stirred for 2 h, and poured onto ice. The mixture was extracted with CH2Cl2 (100 mL), and the organic layer was washed with H2O (50 mL) and brine (50 mL). The solvents were evaporated, and the remaining oil was purified by flash chromatography on silica gel eluting with a EtOAc/hexanes gradient (0% to 20% EtOAc) to provide the desired phenol. To a solution of this phenol in pyridine (10 mL) under argon was slowly added acetic anhydride (0.6 mL, 6.33 mmol). After 2 h, the volatile materials were removed to provide 3-bromo-5-formyl-phenyl acetate (170b, 1.02 g, 40%).
With boron tribromide; In dichloromethane; at -78 - 20℃; for 2h; step 1-A solution of BBr3 (29.1 mL of a 1.0 M solution in DCM, 29.1 mmol) was added slowly to a solution of 45a (2.5 g, 11.62 mmol) in anhydrous DCM (25 mL) maintained under N2 at -78 C. The orange solution was warmed to RT, stirred for 2 h, and poured onto ice. The mixture was extracted with DCM (100 mL), and the organic layer was washed with H2O (50 mL) and brine (50 mL). The solvents were evaporated, and the remaining oil was purified by flash chromatography on SiO2 eluting with an EtOAc/hexane gradient (0% to 20% EtOAc) to provide the desired phenol. To a solution of this phenol in pyridine (10 mL) under argon was slowly added acetic anhydride (0.6 mL, 6.33 mmol). After 2 h, the volatile materials were removed to provide 3-bromo-5-formyl-phenyl acetate (45b, 1.02 g, 40 %).
With boron tribromide; In dichloromethane; at -78 - 20℃; for 2h; A solution of BBr3 (29.1 mL of a 1.0 M solution in DCM, 29.1 mmol) was added slowly to a solution of 62a (2.5 g, 11.62 mmol) in anhydrous DCM (25 mL) maintained under N2 at -78 C. The orange solution was warmed to RT, stirred for 2 h, and poured onto ice. The mixture was extracted with CH2Cl2 (100 mL), and the organic layer was washed with H2O (50 mL) and brine (50 muL). The solvents were evaporated, and the remaining oil was purified by flash chromatography on silica gel eluting with a EtOAc/hexanes gradient (0% to 20% EtOAc) to provide the desired phenol. To a solution of this phenol in pyridine (10 mL) under argon was slowly added acetic anhydride (0.6 mL, 6.33 mmol). After 2 h, the volatile materials were removed to provide 3-bromo-5-formyl-phenyl acetate (62b, 1.02 g, 40%).
With boron tribromide; In dichloromethane; at -78 - 20℃; for 2h; A solution of BBr3 (29.1 mL of a 1.0 M solution in DCM, 29.1 mmol) was added slowly to a solution of R-17a (2.5 g, 11.62 mmol, CAS Reg. No. 262450-65-7) in anhydrous DCM (25 mL) maintained under N2 at -78 C. The orange solution was warmed to RT, stirred for 2 h, and poured onto ice. The mixture was extracted with DCM (100 mL), and the organic layer was washed with H2O (50 mL) and brine (50 mL). The solvents were evaporated, and the remaining oil was purified by SiO2 chromatography eluting with a EtOAc/hexanes gradient (0% to 20% EtOAc) to provide the desired phenol. To a solution of this phenol in pyridine (10 mL) under argon was slowly added acetic anhydride (0.6 mL, 6.33 mmol). After 2 h, the volatile materials were removed to provide 3-bromo-5-formyl-phenyl acetate (R-17b, 1.02 g, 40%).
With boron tribromide; In dichloromethane; at -78 - 20℃; for 2h; step 1-A solution of BBr3 (29.1 mL of a 1.0 M solution in DCM, 29.1 mmol) was added slowly to a solution of R-17a (2.5 g, 11.62 mmol, CASRN 262450-65-7) in anhydrous DCM (25 mL) maintained under N2 at -78 C. The orange solution was warmed to RT, stirred for 2 h, and poured onto ice. The mixture was extracted with DCM (100 mL), and the organic layer was washed with H2O (50 mL) and brine (50 mL). The solvents were evaporated, and the remaining oil was purified by SiO2 chromatography eluting with a EtOAc/hexanes gradient (0% to 20% EtOAc) to provide the desired phenol. To a solution of this phenol in pyridine (10 mL) under argon was slowly added acetic anhydride (0.6 mL, 6.33 mmol). After 2 h, the volatile materials were removed to provide 3-bromo-5-formyl-phenyl acetate (R-17b, 1.02 g, 40%).
A solution of BBr3 (29.1 mL of a 1.0 M solution in CH2Cl2, 29.1 mmol) was added slowly to a solution of 119 (2.5 g, 11.62 mmol) in anhydrous CH2Cl2 (25 mL) under nitrogen at -78 C. The orange solution was warmed to RT, stirred for 2 h, and poured onto ice. The mixture was extracted with CH2Cl2 (100 mL), and the organic layer was washed with H2O (50 mL) and brine (50 mL). The solvents were evaporated, and the remaining oil was purified by flash chromatography on silica gel (0% to 20% EtOAc/hexanes) to provide the desired phenol. To a solution of this phenol in pyridine (10 mL) under argon was slowly added acetic anhydride (0.6 mL, 6.33 mmol). After 2 h, the volatile materials were removed to provide 3-bromo-5-formyl-phenyl acetate (120, 1.02 g, 40%).
With boron tribromide; In dichloromethane; at -78 - 20℃; for 2h; step 1-A solution of BBr3 (29.1 mL of a 1.0 M solution in DCM, 29.1 mmol) was added slowly to a solution of 27a (2.5 g, 11.62 mmol) in anhydrous DCM (25 mL) maintained under N2 at -78 C. The orange solution was warmed to RT, stirred for 2 h, and poured onto ice. The mixture was extracted with DCM (100 mL), and the organic layer was washed with H2O (50 mL) and brine (50 mL). The solvents were evaporated, and the remaining oil was purified by flash chromatography on silica gel eluting with a EtOAc/hexanes gradient (0% to 20% EtOAc) to provide the desired phenol. To a solution of this phenol in pyridine (10 mL) under argon was slowly added acetic anhydride (0.6 mL, 6.33 mmol). After 2 h, the volatile materials were removed to provide 3-bromo-5-formyl-phenyl acetate (27b, 1.02 g, 40%).

  • 25
  • [ 74137-36-3 ]
  • [ 68-12-2 ]
  • [ 262450-65-7 ]
YieldReaction ConditionsOperation in experiment
98% With n-butyllithium; In diethyl ether; at -78℃; for 0.75h; n-BuLi (2.6 mL of a 1.6 M solution, 1.1 equiv) was added slowly to a solution of the 180a (1.0 g, 3.8 mmol) in Et2O (20 mL) cooled to -78 C. under an N2 atmosphere. The solution was stirred for 45 min, and DMF was added via syringe. The solution was warmed slowly to RT, added to saturated ammonium chloride, and extracted with ether. The organic phase was washed with brine and dried (MgSO4), filtered and evaporated to afford 0.80 g (98%) of 180b.
98% Preparation of 3-bromo-5-cyano-phenol (CASRN 770718-92-8) step 1-n-BuLi (2.6 mL of a 1.6 M solution, 1.1 equiv) was added slowly to a solution of the 1,3-dibromo-5-methoxy-benzene (1.0 g, 3.8 mmol, CAS Reg. No. 74137-36-3) in Et2O (20 mL) cooled to -78 C. under an N2 atmosphere. The solution was stirred for 45 min, and DMF was added via syringe. The solution was warmed slowly to RT, added to saturated ammonium chloride, and extracted with ether. The organic phase was washed with brine and dried (MgSO4), filtered and evaporated to afford 0.80 g (98%) of 1-bromo-3-formyl-benzaldehyde.
98% step 1-n-BuLi (2.6 mL of a 1.6 M solution, 1.1 equiv) was added slowly to a solution of the 1,3-dibromo-5-methoxy-benzene (1.0 g, 3.8 mmol, CAS Reg. No. 74137-36-3) in Et2O (20 mL) cooled to -78 C. under an N2 atmosphere. The solution was stirred for 45 min, and DMF was added via syringe. The solution was warmed slowly to RT, added to saturated ammonium chloride, and extracted with ether. The organic phase was washed with brine and dried (MgSO4), filtered and evaporated to afford 0.80 g (98%) of 1-bromo-3-formyl-benzaldehyde.
98% [3-(3-Bromo-5-cyano-phenoxy)-4-chloro-2-fluoro-phenyl]-acetic Acid Ethyl Ester (R-20c) step 1-n-BuLi (2.6 mL of a 1.6 M solution, 1.1 equiv) was added slowly to a solution of the R-21a (1.0 g, 3.8 mmol, CAS Reg. No. 74137-36-3) in Et2O (20 mL) cooled to -78 C. under an N2 atmosphere. The solution was stirred for 45 min, and DMF was added via syringe. The solution was warmed slowly to RT, added to saturated ammonium chloride, and extracted with ether. The organic phase was washed with brine and dried (MgSO4), filtered and evaporated to afford 0.80 g (98%) of R-21b.
98% Example 2 2-(3-(4-Isopropylpiperazin-1-yl)-5-methoxyphenyl)-5,7-dimethoxyquinazolin-4(3H)-one A solution of 1,3-dibromo-5-methoxybenzene (5.00 g, 18.8 mmol) in anhydrous diethyl ether (100 mL) was cooled to -78 C. Then a solution of n-butyllithium in hexanes (2.5 M, 8.3 mL, 20.68 mmol) was added drop-wise at -78 C. under nitrogen. After the addition was complete, the reaction was stirred at -78 C. for 45 min. After that time, anhydrous DMF (7.3 mL), 94.0 mmol) was added, the cooling bath was removed and the reaction mixture was allowed to warm to rt. The reaction was diluted with saturated aqueous NH4Cl solution (100 mL) and diethyl ether (100 mL). The organic phase was separated, washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 3-bromo-5-methoxybenzaldehyde (3.95 g, 98%) as yellow oil: 1H NMR (400 MHz, CDCl3) delta9.90 (s, 1H), 7.57-7.60 (m, 1H), 7.31-7.33 (m, 2H), 3.86 (s, 3H).
96% Step 1 A solution of 1,3-dibromo-5-methoxybenzene (15 g, 56.40 mmol) in anhydrous Et2O (200 ML) under nitrogen was cooled to -78 C. n-BuLi (38.80 ML of a 1.6 M solution in Et2O, 62.00 mmol) was added dropwise, and the solution was aged at -78 C. for 45 m.To the resulting heterogeneous mixture was added anhydrous DMF (4.78 ML, 62.00 mmol), and the solution was slowly warmed to RT. The mixture was poured into H2O (200 ML), and the aqueous phase was extracted with Et2O (3*125 ML).The combined organic fractions were washed with brine (100 ML) and dried over anhydrous MgSO4.Evaporation of the solvent provided 11.70 g (96%) of 3-bromo-5-methoxybenzaldehyde (115)115).
73.2% A solution of 1,3-dibromo-5-methoxybenzene (24.5 g, 92.13 mmol, 1 equiv) in Et2O (400 mL) under nitrogen, cooled to -78 oC and stirred for 20 min was added n-BuLi (2.5mol/L in THF, 44 mL, 1.20 equiv) dropwised at -78 oC. The reaction mixture was continued to stir for 1h at -78 oC followed by addition of DMF (8.1 g, 110.55 mmol, 1.2 equiv) dropwise. After stirring for 45 min at -78oC, the reaction was quenched with water (200 ml) carefully and extracted with EtOAc (500 mL) twice. The combined organic layers were concentrated under reduced pressure to give a mixture, which was further triturated with hexane (200mL) to afford 3-bromo-5-methoxybenzaldehyde (45-2) (14.5 g, 73.2%) as a white solid.
step 2-To a solution of 1,3-dibromo-5-methoxy-benzene (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluding with a hexane/EtOAc gradient (3 to 5% EtOAc) to afford 3-bromo-5-methoxy-benzaldehyde.
To a solution of 1,3-dibromo-5-methoxy-benzene (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluding with a hexane/EtOAc gradient (3 to 5% EtOAc) to afford 3-bromo-5-methoxy-benzaldehyde.
step 2-To a solution of R-27b (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (3 to 5% EtOAc) to afford R-28.
step 2-To a solution of 57b (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (97:3 to 95:5) to afford 58.
step 9-; To a solution of 10b (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (3 to 5% EtOAc) to afford 11.

  • 26
  • [ 557-21-1 ]
  • [ 262450-65-7 ]
  • [ 21962-46-9 ]
YieldReaction ConditionsOperation in experiment
tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 90℃; for 48h; step 3-A solution of <strong>[262450-65-7]3-bromo-5-methoxy-benzaldehyde</strong> (1 mmol) in DMF (2 mL) is added to a round bottomed flask containing Zn(CN)2 (0.7 equivalents), Pd(PPh3)4(0) (0.2 equivalents) in DMF (15 mL). The reaction is stirred at 90 C. under an atmosphere of argon for 48 h. The reaction mixture is cooled and evaporated to dryness. The crude residue is dissolved in EtOAc, washed with brine solution, dried (MgSO4) and evaporated. The crude product is purified by SiO2 chromatography to afford 3-formyl-5-methoxy-benzonitrile.
tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 90℃; for 48h; A solution of <strong>[262450-65-7]3-bromo-5-methoxy-benzaldehyde</strong> (1 mmol) in DMF (2 mL) is added to a round bottomed flask containing Zn(CN)2 (0.7 equivalents), Pd(PPh3)4(0) (0.2 equivalents) in DMF (15 mL). The reaction is stirred at 90 C. under an atmosphere of argon for 48 h. The reaction mixture is cooled and evaporated to dryness. The crude residue is dissolved in EtOAc, washed with brine solution, dried (MgSO4) and evaporated. The crude product is purified by SiO2 chromatography to afford 3-formyl-5-methoxy-benzonitrile.
tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 90℃; for 48h; step 10-; Cyanation of 11 to afford 12a was carried out with Zn(CN)2, Pd(PPh3)4(O) and DMF. A solution of 11 (1 mmol) in DMF (2 mL) is added to a round bottomed flask containing Zn(CN)2 (0.7 equivalents), Pd(PPh3)4(O) (0.2 equivalents) in DMF (15 mL). The reaction is stirred at 90 C. under an atmosphere of argon for 48 h. The reaction mixture is cooled and evaporated to dryness. The crude residue is dissolved in EtOAc, washed with brine solution, dried (MgSO4) and evaporated. The crude product is purified by SiO2 chromatography
  • 27
  • [ 60-29-7 ]
  • [ 74137-36-3 ]
  • [ 262450-65-7 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; In hexane; at -78℃; for 0.833333h; To a solution of 20b (60 g, 0.2256 mol) and anhydrous Et2O (1 L)cooled to -78° C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78° C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78° C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30° C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10° C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (3 to 5percent EtOAc) to afford 21.
  • 28
  • [ 73963-98-1 ]
  • [ 262450-65-7 ]
  • [ 21962-46-9 ]
YieldReaction ConditionsOperation in experiment
tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 80℃; for 5.5h; A solution of 21 (10 g, 31.7 mmol), Pd[P(Ph)3]4(0) (2.62 g, 2.26 mmol), Zn(CN)2(2.24 g, 19.0 mmol) and DMF (100 mL) under a N2 atmosphere is heated to 80 C. for 5.5 h. The reaction mixture is cooled to RT and is partitioned between water and DCM. The DCM extracts are washed with water and brine and is dried (MgSO4). The crude product is purified by SiO2 chromatography eluting with EtOAc/hexane to afford 22a.
  • 29
  • [ 262450-65-7 ]
  • [ 98-80-6 ]
  • [ 1073643-48-7 ]
  • 30
  • [ 110-89-4 ]
  • [ 262450-65-7 ]
  • [ 1200131-21-0 ]
YieldReaction ConditionsOperation in experiment
69% To a pre-stirred solution of <strong>[262450-65-7]3-bromo-5-methoxybenzaldehyde</strong> (0.56 g, 2.61 mmol) and piperidine (0.29 mL, 3.93 mmol) in DCM (10 mL) at 0 C was added sodium borohydride (197 mg, 5.22 mmol) in portions. The reaction mixture was allowed to warm to ambient temperature and stirred for an additional 2 h. The reaction was quenched by the addition of water (30 mL) and extracted into ethyl acetate (75 mL) then washed with water (50 mL) then the organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as a colourless oil (510 mg, 69%) that was used in the next step without further purification. 1H NMR (CDCl3, 400MHz): 7.08-7.06 (m, 1H), 6.94-6.91 (m, 1H), 6.83-6.80 (s, 1H), 3.79 (s, 3H), 3.39 (s, 2H), 2.40-2.30 (s, 4H), 1.61-1.51 (m, 4H), 1.47-1.38 (m, 2H).
  • 31
  • [ 110-86-1 ]
  • [ 59649-56-8 ]
  • [ 5970-45-6 ]
  • [ 262450-65-7 ]
  • [ 1237438-52-6 ]
  • 32
  • [ 262450-65-7 ]
  • [ 262450-64-6 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; ethanol; In tetrahydrofuran; at 20℃; for 3h;Cooling with ice; NaBH4 (3.85 g; WAKO) was added to an ethanol (80 mL) and THF (20 mL) mixture solution of <strong>[262450-65-7]3-bromo-5-methoxybenzaldehyde</strong> (22 g) with ice cooling and the resulting mixture was stirred at room temperature for 3 hours. The resulting mixture was poured into ice water (300 mL) and ethyl acetate (300 mL) was added thereto to extract the mixture with and the organic layer was washed with saturated aqueous sodium bicarbonate solution (300 mL) and then dried. The solvent was evaporated under reduced pressure to give the title compound (22.05 g).(Intermediate 1 Rf (TLC)=0.6 (Hex:EtOAc=1:1))
  • 33
  • [ 262450-65-7 ]
  • [ 1343456-53-0 ]
  • 34
  • [ 262450-65-7 ]
  • [ 1343456-54-1 ]
  • 35
  • [ 94-09-7 ]
  • [ 262450-65-7 ]
  • [ 1343456-51-8 ]
YieldReaction ConditionsOperation in experiment
34% In ethanol; for 2h;Reflux; Example 662- (3 -Methoxy-5-morpholin-4-yl-phenyl)-3 ,3 -dimethyl- 1 ,2,3 ,4-tetrahydro-quinoline-6- carboxylic acidA mixture of 4-amino-benzoic acid ethyl ester (6.1 g, 36.9 mmol) and 3-bromo-5- methoxy-benzaldehyde (8.0 g, 36.9 mmol) in ethanol (100 mL) was prepared. The reaction mixture was heated to reflux for 2 hours. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 4-[l-(3-bromo-5-methoxy-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (4.5 g, 34%) as a white solid: LC/MS m/e calcd for Ci7Hi6BrN03 M+: 362.2, observed: 362.1.
34% In ethanol; for 2h;Reflux; A mixture of 4-amino-benzoic acid ethyl ester (6.1 g, 36.9 mmol) and <strong>[262450-65-7]3-bromo-5-methoxy-benzaldehyde</strong> (8.0 g, 36.9 mmol) in ethanol (100 mL) was prepared. The reaction mixture was heated to reflux for 2 hours. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 4-[1-(3-bromo-5-methoxy-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (4.5 g, 34%) as a white solid: LC/MS m/e calcd for C17H16BrNO3 M+: 362.2, observed: 362.1
 

Historical Records

Technical Information

• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nomenclature of Ethers • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Ethers • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reactions of Ethers • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

Related Functional Groups of
[ 262450-65-7 ]

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