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Chemical Structure| 16657-07-1 Chemical Structure| 16657-07-1

Structure of 16657-07-1

Chemical Structure| 16657-07-1

7-Bromo-1H-indene

CAS No.: 16657-07-1

4.5 *For Research Use Only !

Cat. No.: A211598 Purity: 98%

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Product Details of [ 16657-07-1 ]

CAS No. :16657-07-1
Formula : C9H7Br
M.W : 195.06
SMILES Code : BrC1=CC=CC2=C1CC=C2
MDL No. :MFCD16652275
InChI Key :JTRQKQGKIYROIO-UHFFFAOYSA-N
Pubchem ID :13330209

Safety of [ 16657-07-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 16657-07-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.11
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 47.08
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.36
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

3.4
Log Po/w (WLOGP)?

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

2.91
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.

3.5
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

3.4
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.11

Water Solubility

Log S (ESOL):?

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

-3.64
Solubility 0.0452 mg/ml ; 0.000232 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.

-3.08
Solubility 0.162 mg/ml ; 0.000833 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

-3.62
Solubility 0.0473 mg/ml ; 0.000243 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

Low
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.

-5.08 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

2.0
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

0.0 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)

2.54

Application In Synthesis of [ 16657-07-1 ]

* 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 [ 16657-07-1 ]

[ 16657-07-1 ] Synthesis Path-Downstream   1~33

  • 2
  • [ 16657-07-1 ]
  • [ 75-16-1 ]
  • [ 7372-92-1 ]
  • 3
  • [ 16657-07-1 ]
  • EtMgX [ No CAS ]
  • [ 92013-13-3 ]
  • 4
  • [ 16657-07-1 ]
  • n-PrMgX [ No CAS ]
  • [ 92013-14-4 ]
  • 5
  • [ 16657-07-1 ]
  • n-BuMgX [ No CAS ]
  • [ 92013-15-5 ]
  • 6
  • [ 90725-40-9 ]
  • [ 16657-07-1 ]
  • 7
  • [ 66192-11-8 ]
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  • [ 15115-58-9 ]
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  • 10
  • [ 58380-12-4 ]
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  • [ 824-22-6 ]
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  • [ 66256-38-0 ]
  • 13
  • [ 16657-07-1 ]
  • [ 92013-16-6 ]
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  • [ 16657-07-1 ]
  • [ 92013-17-7 ]
  • 15
  • [ 3433-80-5 ]
  • [ 16657-07-1 ]
  • 16
  • [ 14647-23-5 ]
  • [ 16657-07-1 ]
  • [ 920-39-8 ]
  • [ 535969-39-2 ]
YieldReaction ConditionsOperation in experiment
88% With ammonium chloride; In tetrahydrofuran; water; (1) Synthesis of 7-isopropylindene Using a 300 ml three-necked flask as the reactor, under a nitrogen stream, 1.36 g (2.57 millimoles) of [1,2-bis (diphenylphosphino)ethane]dichloronickel(II) was dissolved in 20 ml of tetrahydrofuran. To this suspension there was added a solution of 10 g (51.30 millimoles) of <strong>[16657-07-1]7-bromoindene</strong> in 100 ml of tetrahydrofuran, prepared based on the method described in J. Org. Chem. 49, 4226-4237(1984). After dropwise addition of 51 ml (102.60 millimoles) of isopropylmagnesium bromide (2N) to the mixed solution while cooling on ice, the mixture was heated to reflux for 20 hours. After reflux, hydrolysis was performed with a saturated aqueous solution of ammonium chloride, distilled water was added, extraction was performed several times with diethyl ether, and then the extract was washed once with saturated saline and dried over anhydrous magnesium sulfate. After drying, the magnesium sulfate was filtered off and the solvent was purified with a silica gel column to obtain 7.14 g of 7-isopropylindene as a yellow oil (88% yield).
  • 17
  • [ 98-29-3 ]
  • [ 16657-10-6 ]
  • [ 104-15-4 ]
  • [ 16657-07-1 ]
YieldReaction ConditionsOperation in experiment
In toluene; Stage A: 4-bromo-3H-indene 30 g of 4-bromo-1-indanol is dissolved in 720 ml of toluene, 27 g of paratoluene sulphonic acid is added, then 0.93 g of 4-tertbutylcatechol is added. The mixture is taken to reflux for one hour. After cooling to 20 C., the organic phase is washed with 25 ml of N sodium hydroxide, dried and concentrated to dryness, and the residue is chromatographed on silica, eluding with a hexane-difluoro dichloro ethane mixture (95-5), and 24.6 g of expected product is isolated. Aromatic 1544 cm-1
  • 18
  • tetrabutylammonium hydrogenosulphate [ No CAS ]
  • [ 16657-07-1 ]
  • [ 937-14-4 ]
  • 4-bromo-1,2-epoxyindene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; Stage A: 4-bromo-1,2-epoxyindene 250 ml of pH 8 phosphate buffer, 150 ml of methylene chloride, 200 mg of tetrabutylammonium hydrogenosulphate and 10 g of <strong>[16657-07-1]4-bromo-3H-indene</strong> are mixed together. At 0 C. 10 g of metachloroperbenzoic acid is added in several lots, then the temperature of the mixture is allowed to rise to the ambient over 4 hours, 10 g of metachloroperbenzoic acid is added at 0 C. and the temperature is allowed to rise to 20 C. over 2 hours. 3 g of metachloroperbenzoic acid is added and the mixture is left for 16 hours at ambient temperature, then decanted and extracted with methylene chloride; the extracts are washed with water, with a thiosulphate solution and with water, dried and evaporated to dryness. The residue is chromatographed on silica, eluding with a mixture of hexane and isopropyl ether (9-1) with 3% of triethylamine, and 4.11 g of expected product is isolated.
  • 19
  • LiN[Si(CH3)3 ]2 [ No CAS ]
  • bis(2-chloroethyl)-tert-butyl carbamate [ No CAS ]
  • [ 16657-07-1 ]
  • 1'-(2-Hydroxy-1,2,3,4-tetrahydronaphth-3-yl)-spiro[4-bromo-1H-indene-1,4'-piperidine] Hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
1'-(2-Hydroxy-1,2,3,4-tetrahydronaphth-3-yl)-spiro[4-bromo-1H-indene-1,4'-piperidine] Hydrochloride (15) The reaction of <strong>[16657-07-1]7-bromo-1H-indene</strong> (3.50 g, 17.94 mmol) with LiN[Si(CH3)3 ]2 and bis(2-chloroethyl)-tert-butyl carbamate (Procedure H) yielded a mixture of two products (5.85 g, 90%) in a ratio of 85:15, respectively, as revealed by HPLC (silica gel, 2% acetone-hexanes). Deprotection (see 21a), subsequent neutralization and extraction into EtOAc yielded, after concentration, 2.2 g (46%) of the crude free base. Trituration of this residue with CH2 Cl2 yielded 27 as a white solid which was collected by filtration, washed with CH2Cl2 and dried at 50 C. in vacuo; mp 310-315 C. (sinters); 1 H NMR (DMSOd6)delta1.30 (d, 2, piperidyl alpha-Heq, J=13.5 Hz), 2.38 (dt, 2, piperidyldelta-Hax, J=12.9 Hz, J'=4.8 Hz), 3.21 (dt, 2, piperidyl alpha-Hax, J=13.4 Hz, J'=2.4 Hz), 3.35 (d, 2, piperidyl alpha-Heq, J=11.1 Hz), 6.78 (d, 1, indenyl C2-H, J=6.0 Hz), 7.14 (t, 1, indenyl C6-H, J=8.4 Hz), 7.26 (d, 1, indenyl C2-H, J=6.0 Hz), 7.29 (d, 1, indenyl C5-H, J=6.0 Hz), 7.40 (d, 1, indenyl C7-H, J=8.4 Hz). A soln of 1M Et3 Al in toluene (0.65 mL) was added dropwise at room temperature, under N2, to a stirring suspension of 27 (0.30 g, 1.13 mmol) in CH2 Cl2 (13 mL). Complete dissolution occurred at the end of the addition. The resulting soln was stirred at r.t. for 40 min at which time a soln of 1,4-dihydronaphthalene oxide in CH2 Cl2 (5 mL), prepared from the corresponding bromohydrin (1.35 mmol) as described in Procedure B above, was added dropwise over 5 min. Stirring was contd for 21 h. The reaction was quenched by dropwise addition of 4N NaOH (20 mL). The resulting mixture was stirred vigorously for 2 h, diluted with H2 O (25 mL) and extracted with CH2 Cl2 (3*30 mL). The combined organic extracts were dried over NaSO4 and conc to a tan solid which was purified by radial flow chromatography on silica gel (hexanes,79:acetone,20:Et3 N,1) to yield an off-white solid (0.30 g, 65%); mp 265-267 C.; 1 H NMR (CDCl3)delta1.45 (d, 2, piperidyl beta-Heq, J=12.9 Hz), 2.10-2.28 (m, 2, piperidyl alpha-Hax), 2.65 (t, 1, piperidyl alpha-Hax, J=11.4 Hz), 2.81-3.11 (m, 7, tetrahydronaphthyl C1-H, C4-H & piperidyl), 3.35 (dd, 1, piperidyl a-Heq, J=16.1 Hz, J'=5.7 Hz), 3.93 (m, 1, CHOH), 6.87 (d, 1, indenyl C2-H, J=5.7 Hz), 6.96 (d, 1, indenyl C3-H, J=5.7 Hz), 7.12 (m, 5, aryl), 7.31 (d, 1, indenyl C5-H, J=7.4 Hz), 7.38 (d, 1, indenyl C7-H, J=7.9 Hz).
  • 20
  • [ 4045-44-7 ]
  • [ 16657-07-1 ]
  • iron(II) chloride [ No CAS ]
  • [ 938439-73-7 ]
  • 22
  • [ 16657-07-1 ]
  • [ 846032-36-8 ]
YieldReaction ConditionsOperation in experiment
PREPARATIVE EXAMPLE 34; In a manner similar to that previously described (e.g. Example 1), 4-bromo-1- indanone was converted to 4-bromo-2-indanone (34A) and then further to (+/-)-34F (LCMS m/z 267/269, MH+).
  • 23
  • [ 16657-07-1 ]
  • [ 125114-82-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; 3-bromo-1,2-bis(bromomethyl)benzene; In dichloromethane; at 20℃;Cooling with ice;Product distribution / selectivity; Another alternative conversion of 34A to 34B is described below: To an ice-cooled mixture of the 34A (crude, 22g, 0.113 mol) in DCM (360 mL) was added sodium bicarbonate (28.5g, 0.339 mol) followed by mCPBA (35.4g, 0.16 mol) portionwise. The reaction was slowly warmed to RT and vigorously stirred for 4 h. The mixture was quenched/washed with 10% solution of aq sodium sulfite followed by a final wash with brine. The organic phase was dried over anhydrous sodium sulfate and concentrated to dryness to provide 34G (100%).
  • 24
  • [ 16657-10-6 ]
  • [ 16657-07-1 ]
  • [ 45738-35-0 ]
YieldReaction ConditionsOperation in experiment
69% With sulfuric acid; In water;Reflux; [00163] 4-Bromo-lH-indene (d): Compound c (150 g, 704 mmol, 1 equiv) was suspended in a mixture of concentrated sulfuric acid (250 mL) and water (1.25 L). The mixture was refluxed overnight. The reaction was cooled and extracted with 1.5 L of dichloromethane. The organic layer was washed with saturated sodium bicarbonate (1.5 L), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified over silica gel (800 g), eluting with heptanes to give compound d (95 g, 69% yield) as a light yellow oil.
With sulfuric acid; In water;Reflux; 4-Bromo-1H-indene (4): Compound 3 (150 g, 704 mmol, 1 equiv) was suspended in a mixture of concentrated sulfuric acid (250 mL) and water (1.25 L). The mixture was refluxed overnight. The reaction was cooled and extracted with 1.5 L of dichloromethane. The organic layer was washed with saturated sodium bicarbonate (1.5 L), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified over silica gel (800 g), eluting with heptanes to give compound 4 (95 g, 69% yield) as a light yellow oil.
  • 25
  • η6-(naphtalene)(η5-cyclopentadienyl)-iron(II) hexafluorophosphate [ No CAS ]
  • [ 16657-07-1 ]
  • [ 1450822-68-0 ]
  • 26
  • [ 54380-53-9 ]
  • [ 16657-07-1 ]
  • (4-bromo-2,3-dihydro-1H-inden-2-yl)trimethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tris(pentafluorophenyl)borate; In dichloromethane; at 20℃; for 17h;Glovebox; Inert atmosphere; General procedure: In glove box, a 1.3-mL GLC vial is charged with B(C6F5)3 (5.0 mol%) and a magnetic stir bar. Into a separatevial are weighed the alkene (1.0 equiv) and the cyclohexa-2,5-dien-1-ylsilane (1.3 equiv). Both reagents are dissolvedin CH2Cl2 (1.0M) and the resulting solution is added to the catalyst. The vial is then capped, and the solution is stirredin the glove box. The reaction is monitored by GLC and typically requires 15 to 24 h stirring at room temperature. Themixture is finally diluted with n-pentane (0.3 mL), filtered over a small Celite/SiO2 column (1 cm Celite covered with0.5 cm SiO2, eluting with n-pentane), and all volatiles are removed under reduced pressure. If necessary, the crudetarget compound is purified by either flash column chromatography or Kugelrohr distillation.Prepared according to GP2 from <strong>[16657-07-1]7-bromo-1H-indene</strong> (39.0 mg, 0.20 mmol, 1.0 equiv) and cyclohexa-2,5-dien-1-yltrimethylsilane (39.6 mg, 0.26 mmol, 1.3 equiv). Conversion was complete after 17 h. Purified by Kugelrohr distillation (10 mbar, 150C). Colorless oil, 35 mg, 65% yield. IR (ATR): /cm-1 = 2952, 2894, 2837, 1567, 1447, 1319, 1248, 1162, 1137, 1117, 1057, 987, 914, 831, 763, 689. 1H NMR (500 MHz, C6D6) delta = 7.25 (d, J = 7.9, 1 H), 6.88 (d, J = 7.3, 1 H), 6.74 (t, J = 7.6, 1 H), 3.03 (dd, J = 16.3, 9.1, 1 H), 2.73 (dt, J = 16.1, 9.9, 2H), 2.59 (dd, J = 15.9, 10.7, 1 H), 1.26 (p, J = 9.8, 1 H), -0.11 (s, 9H). 13C NMR (126 MHz, C6D6) delta = 147.1, 145.5, 129.6, 128.3, 123.2, 120.3, 36.6, 36.1, 25.2, -3.1 (3C). GLC-MS (EI) for (C12H17BrSi): m/z 270.0 [M]+, 255.0 [M-CH3]+. HRMS (EI) exact mass for [M]+: calcd m/z 268.02774, found 268.02740.
  • 27
  • [ 71597-85-8 ]
  • [ 16657-07-1 ]
  • [ 1279015-90-5 ]
YieldReaction ConditionsOperation in experiment
7-Bromo-1H-indene (250 mg, 1.28 mmol), 4-hydroxyphenylboronic acid (212 mg, 1.54 mmol), sodium carbonate (270 mg, 2.56 mmol), Pd(PPh3)4 (catalytic amount), 1,4-dioxane (10 mL), and water (3 mL) were added, and stirred at 90 C for 8 hours. The solvent was distilled away under reduced pressure. Ethyl acetate was used as an extraction solvent, and after washing with a 1 N hydrochloric acid aqueous solution and saturated brine, the resultant was dried over magnesium sulfate. The solvent was distilled away under reduced pressure. To half of the resulting residue, methanol (10 mL) and a catalytic amount of 10% palladium-carbon were added, and stirred in a hydrogen atmosphere at room temperature overnight. The insoluble material was filtered off, and the solvent was distilled away under reduced pressure. An operation similar to that in Step 2 of Example 9 was performed on the resulting residue to thus obtain the title compound. Yield: 3.1 mg (0.007 mmol) MS (ESI, m/z) 442 [M+H]+
  • 28
  • [ 15115-58-9 ]
  • [ 16657-07-1 ]
  • [ 45738-35-0 ]
  • 29
  • [ 15115-60-3 ]
  • [ 16657-07-1 ]
  • [ 45738-35-0 ]
  • 30
  • potassium phosphate [ No CAS ]
  • [ 16657-07-1 ]
  • [ 603-35-0 ]
  • 3-tert-butylphenylboronic acid [ No CAS ]
  • 4-(3-t-butylphenyl)indene [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With dichlorobis(triphenylphosphine)palladium[II]; In 1,2-dimethoxyethane; (1) Synthesis of 4-(3-t-butylphenyl)indene 40.4 g (205 mmol) of tripotassium phosphate, 200 mL of distilled water, 200 mL of DME, 21.9 g (123 mmol) of 3-t-butylphenylboronic acid, 20.0 g (102 mmol) of <strong>[16657-07-1]7-bromo-1H-indene</strong>, 720 mg (1.02 mmol) of dichlorobis(triphenylphosphine)palladium, and 537 mg (2.05 mmol) of triphenyl phosphine were put into a 500-mL glass reactor in that order, and then heated under reflux at 90 C. for 15 hours. This was left cooled to room temperature, transferred into a separatory funnel, and extracted three times with ethyl acetate. The ethyl acetate solution was washed three times with saturated saline water, and dried with sodium sulfate. Sodium sulfate was filtered away, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent, petroleum ether) to give 22.7 g (yield 89%) of 4-(3-t-butylphenyl)indene as a yellow oil.
  • 31
  • potassium phosphate [ No CAS ]
  • [ 16657-07-1 ]
  • [ 603-35-0 ]
  • [ 183158-34-1 ]
  • 4-(2,3-dimethylphenyl)indene [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With dichlorobis(triphenylphosphine)palladium[II]; In 1,2-dimethoxyethane; (1) Synthesis of 4-(2,3-dimethylphenyl)indene 38 g (180 mmol) of tripotassium phosphate, 100 mL of distilled water, 100 mL of DME, 10 g (66.7 mmol) of 2,3-dimethylphenylboronic acid, 10.8 g (55.4 mmol) of <strong>[16657-07-1]7-bromo-1H-indene</strong>, 1.0 g (1.42 mmol) of dichlorobis(triphenylphosphine)palladium, and 1.30 g (4.96 mmol) of triphenyl phosphine were put into a 500-mL glass reactor in that order, and then heated under reflux at 90 C. for 11 hours. This was left cooled to room temperature, and the reaction liquid was poured into 100 mL of distilled water, transferred into a separatory funnel, and extracted three times with hexane. 6 mL of concentrated hydrochloric acid was added to the hexane solution at room temperature, then stirred at room temperature for 30 minutes, the palladium compound was precipitated, filtered away through filter paper, and the filtrate was washed three times each with saturated saline water and distilled water, and then dried with sodium sulfate. Sodium sulfate was filtered away, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent, hexane/diisopropyl ether=20/1) to give 11.66 g (yield 96%) of 4-(2,3-dimethylphenyl)indene as a colorless oil.
  • 32
  • potassium phosphate [ No CAS ]
  • [ 17933-03-8 ]
  • [ 16657-07-1 ]
  • [ 603-35-0 ]
  • 4-(3-methylphenyl)indene [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With dichlorobis(triphenylphosphine)palladium[II]; In 1,2-dimethoxyethane; (1) Synthesis of 4-(3-methylphenyl)indene 38 g (180 mmol) of tripotassium phosphate, 100 mL of distilled water, 100 mL of DME, 10 g (73.6 mmol) of 3-methylphenylboronic acid, 12.0 g (61.5 mmol) of <strong>[16657-07-1]7-bromo-1H-indene</strong>, 323 mg (0.460 mmol) of dichlorobis(triphenylphosphine)palladium, and 432 mg (1.65 mmol) of triphenyl phosphine were put into a 500-mL glass reactor in that order, and then heated under reflux at 90 C. for 8 hours. This was left cooled to room temperature, then the reaction liquid was poured into 100 mL of distilled water, transferred into a separatory funnel, and extracted three times with hexane. At room temperature 6 mL of concentrated hydrochloric acid was added to the hexane solution, then stirred at room temperature for 30 minutes, the palladium compound was precipitated, filtered out through filter paper, and the filtrate was washed three times each with saturated saline water and distilled water, and dried with sodium sulfate. Sodium sulfate was filtered away, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent, hexane/diisopropyl ether=20/1) to give 12.7 g (yield 100%) of 4-(3-methylphenyl)indene as a colorless oil.
  • 33
  • potassium phosphate [ No CAS ]
  • [ 16419-60-6 ]
  • [ 16657-07-1 ]
  • [ 603-35-0 ]
  • 4-(2-methylphenyl)indene [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With dichlorobis(triphenylphosphine)palladium[II]; In 1,2-dimethoxyethane; (1) Synthesis of 4-(2-methylphenyl)indene 38 g (180 mmol) of tripotassium phosphate, 100 mL of distilled water, 100 mL of DME, 10 g (73.6 mmol) of 2-methylphenylboronic acid, 12.0 g (61.5 mmol) of <strong>[16657-07-1]7-bromo-1H-indene</strong>, 1.00 g (1.42 mmol) of dichlorobis(triphenylphosphine)palladium, and 1.30 g (4.96 mmol) of triphenyl phosphine were put into a 500-mL glass reactor in that order, and then heated under reflux at 90 C. for 11 hours. This was left cooled to room temperature, then the reaction liquid was poured into 100 mL of distilled water, transferred into a separatory funnel, and extracted three times with hexane. At room temperature 6 mL of concentrated hydrochloric acid was added to the hexane solution, then stirred at room temperature for 30 minutes, the palladium compound was precipitated, filtered out through filter paper, and the filtrate was washed three times each with saturated saline water and distilled water, and dried with sodium sulfate. Sodium sulfate was filtered away, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent, hexane/diisopropyl ether=20/1) to give 12.7 g (yield 100%) of 4-(2-methylphenyl)indene as a colorless oil.
 

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