14922-91-9|5-Bromo-2-ethylaniline| Ambeed

Structure of 14922-91-9

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Quality Control of [ 14922-91-9 ] Purity: 98% SDS Specification

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Product Details of [ 14922-91-9 ]

CAS No. :	14922-91-9
Formula :	C₈H₁₀BrN
M.W :	200.08
SMILES Code :	NC1=CC(Br)=CC=C1CC
MDL No. :	MFCD15474855
InChI Key :	LSDOCARYQOKKKP-UHFFFAOYSA-N
Pubchem ID :	23346756

Safety of [ 14922-91-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Computational Chemistry of [ 14922-91-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	1
Num. H-bond acceptors	0.0
Num. H-bond donors	1.0
Molar Refractivity	48.32
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.12
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.73
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.6
Log P_o/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.	2.88
Log P_o/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	2.57
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.58

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.18
Solubility	0.133 mg/ml ; 0.000663 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.	-2.93
Solubility	0.235 mg/ml ; 0.00117 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	-3.69
Solubility	0.0411 mg/ml ; 0.000206 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.	-5.58 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	1.0
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)	1.3

Application In Synthesis of [ 14922-91-9 ]

* 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 [ 14922-91-9 ]

[ 14922-91-9 ] Synthesis Path-Downstream 1~35

Yield	Reaction Conditions	Operation in experiment
		Compounds of formula II which may be mentioned are: 1-aminonaphthalene, 2,5-dimethoxyaniline, 2,5-dipropoxyaniline, 2,5-diethoxyaniline, 2-ethyl-5-bromoaniline, 2-methoxy-5-methylaniline, 2- or 3-methylaniline, 2- or 3-ethylaniline, 2- or 3-chloroaniline, ...

2
[ 10342-66-2 ]
[ 14922-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	With water; tin(ll) chloride; In ethanol; at 70℃; for 2h;	To a solution of 2-ethyl-5-bromo nitrobenzene (9.71 g, 230 mmol) in ethanol (125 ml) is added tin(ll) chloride dihydrate (35.72 g, 225.71 mmol), followed by heating at 70 0C for 2 hours. After cooling to room temperature the solution is poured into crushed ice (1 litre) then diluted with ethyl acetate (200 ml). Solid sodium carbonate is cautiously added until pH 7 is achieved, at which stage the viscous mixture is filtered through diatomaceous earth (further washing with ethyl acetate/aqueous sodium carbonate) and the phases separated. After additional extraction of the aqueous phase, all organic phases are combined, dried over anhydrous magnesium sulfate then concentrated in vacuo. The crude oil is purified by flash column chromatography on silica gel (hexane / ethyl acetate 8:2 ratio) to afford 5-bromo-2- ethylaniline (7.89 g) as a brown oil.
	With water; ammonium chloride; zinc; In methanol; for 1h;Reflux;	Step 3A solution of ammonium chloride (12.5 g, 0.2 mol) in water (30 ml) is added to a mixture of zinc dust (35. 7 g, 0.5 mol) and 4-bromo-1-ethyl-2-nitrobenzene (18 g, 0.07 mol) in methanol (720 ml) and water (180 ml). The reaction mixture is refluxed for one hour, then cooled to room temperature and filtered through a plug of diatomaceous earth. The filtrate is concentrated in vacuo, then diluted with water and extracted with ethyl acetate. The combined organic extracts are washed with water and brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo to yield 5-bromo-2-ethylaniline (14 g), used without further purification in the next step.
		Step 1 : Preparation of 5-bromo-2-ethylanilineTo a solution of 2-ethyl-5-bromo nitrobenzene (9.71 g, 230 mmol) in ethanol (125 ml) is added tin(ll) chloride dihydrate (35.72 g, 225.71 mmol), followed by heating at 70 0C for 2 hours. After cooling to room temperature the solution is poured into crushed ice (1 litre) then diluted with ethyl acetate (200 ml). Solid sodium carbonate is cautiously added until pH 7 is achieved, at which stage the viscous mixture is filtered through diatomaceous earth (further washing with ethyl acetate/aqueous sodium carbonate) and the phases separated. After additional extraction of the aqueous phase, all organic phases are combined, dried over anhydrous magnesium sulfate then concentrated in vacuo. The crude oil is purified by flash column chromatography on silica gel (hexane / ethyl acetate 8:2 ratio) to afford 5-bromo-2-ethylaniline (7.89 g) as a brown oil.

		Example 2Preparation of 2-(4'-chloro-4-ethyl-2'-methylbiphen-3-yl)-4,4-dimethylcyclohexane-1,3-dioneStep 1: Preparation of 5-bromo-2-ethylanilineTo a solution of 2-ethyl-5-bromo nitrobenzene (9.71 g, 230 mmol) in ethanol (125 ml) is added tin(II) chloride dihydrate (35.72 g, 225.71 mmol), followed by heating at 70 C. for 2 hours. After cooling to room temperature the solution is poured into crushed ice (1 litre) then diluted with ethyl acetate (200 ml). Solid sodium carbonate is cautiously added until pH 7 is achieved, at which stage the viscous mixture is filtered through diatomaceous earth (further washing with ethyl acetate/aqueous sodium carbonate) and the phases separated. After additional extraction of the aqueous phase, all organic phases are combined, dried over anhydrous magnesium sulfate then concentrated in vacuo. The crude oil is purified by flash column chromatography on silica gel (hexane/ethyl acetate 8:2 ratio) to afford 5-bromo-2-ethylaniline (7.89 g) as a brown oil.
	With ammonium chloride; zinc; In methanol; water; for 1h;Heating / reflux;	A solution of ammonium chloride (12.5 g, 0.2 mol) in water (30 ml) is added to a mixture of zinc dust (35. 7 g, 0.5 mol) and 4-bromo-1-ethyl-2-nitrobenzene (18 g, 0.07 mol) in methanol (720 ml) and water (180 ml). The reaction mixture is refluxed for one hour, then cooled to room temperature and filtered through a plug of diatomaceous earth. The filtrate is concentrated in vacuo, then diluted with water and extracted with ethyl acetate. The combined organic extracts are washed with water and brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo to yield 5-bromo-2-ethylaniline (14 g), used without further purification in the next step.
	With ammonium chloride; zinc; In methanol; water; for 1h;Heating / reflux;	Step 3 <n="170"/>A solution of ammonium chloride (12.5 g, 0.2 mol) in water (30 ml) is added to a mixture of zinc dust (35. 7 g, 0.5 mol) and 4-bromo-1-ethyl-2-nitrobenzene (18 g, 0.07 mol) in methanol (720 ml) and water (180 ml). The reaction mixture is refluxed for one hour, then cooled to room temperature and filtered through a plug of diatomaceous earth. The filtrate is concentrated in vacuo, then diluted with water and extracted with ethyl acetate. The combined organic extracts are washed with water and brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo to yield 5-bromo-2-ethylaniline (14 g), used without further purification in the next step.
		Step 1 : Preparation of 5-bromo-2-ethylanilineTo a solution of 2-ethyl-5-bromo nitrobenzene (9.71 g, 230 mmol) in ethanol (125 ml) is added tin(ll) chloride dihydrate (35.72 g, 225.71 mmol), followed by heating at 70 0C for 2 hours. After cooling to room temperature the solution is poured into crushed ice (1 litre) then diluted with ethyl acetate (200 ml). Solid sodium carbonate is cautiously added until pH 7 is achieved, at which stage the viscous mixture is filtered through diatomaceous earth (further washing with ethyl acetate/aqueous sodium carbonate) and the phases separated. After additional extraction of the aqueous phase, all organic phases are combined, dried over anhydrous magnesium sulfate then concentrated in vacuo. The crude oil is purified by flash column chromatography on silica gel (hexane / ethyl acetate 8:2 ratio) to afford 5-bromo-2-ethylaniline (7.89 g) as a brown oil
		To a solution of 2-ethyl-5-bromo-1 -nitrobenzene (9.71 g, 230 mmol) in ethanol (125 ml) is added tin(ll) chloride dihydrate (35.72 g, 225.71 mmol), followed by heating at 70 0C for 2 hours. After cooling to room temperature the solution is poured into crushed ice (1 litre) then diluted with ethyl acetate (200 ml). Solid sodium carbonate is cautiously added until pH 7 is achieved, at which <n="39"/>stage the viscous mixture is filtered through diatomaceous earth (further washing with ethyl acetate/aqueous sodium carbonate) and the phases separated. After additional extraction of the aqueous phase, all organic phases are combined, dried over anhydrous magnesium sulfate then concentrated in vacuo. The crude oil is purified by flash column chromatography on silica gel (hexane / ethyl acetate 8:2 ratio) to afford 5-bromo-2-ethylaniline (7.89 g) as a brown oil.
		To a solution of 2-ethyl-5-bromo-1 -nitrobenzene (9.71 g, 230 mmol) in ethanol (125 ml) is added tin(ll) chloride dihydrate (35.72 g, 225.71 mmol), followed by heating at 70 0C for 2 hours. After cooling to room temperature the solution is poured into crushed ice (1 litre) then diluted with ethyl acetate (200 ml). Solid sodium carbonate is cautiously added until pH 7 is achieved, at which stage the viscous mixture is filtered through diatomaceous earth (further washing with ethyl acetate/aqueous sodium carbonate) and the phases separated. After additional extraction of the <n="39"/>aqueous phase, all organic phases are combined, dried over anhydrous magnesium sulfate then concentrated in vacuo. The crude oil is purified by flash column chromatography on silica gel (hexane / ethyl acetate 8:2 ratio) to afford 5-bromo-2-ethylaniline (7.89 g) as a brown oil.

References: [1]Patent: WO2008/71405,2008,A1 .Location in patent: Page/Page column 62.
[2]Patent: WO2010/46194,2010,A1 .Location in patent: Page/Page column 66.
[3]Patent: WO2011/6543,2011,A1 .Location in patent: Page/Page column 48-49.
[4]Patent: US2012/190545,2012,A1 .Location in patent: Page/Page column 23.
[5]Patent: WO2008/110307,2008,A1 .Location in patent: Page/Page column 71.
[6]Patent: WO2008/110308,2008,A2 .Location in patent: Page/Page column 169.
[7]Patent: WO2008/145336,2008,A1 .Location in patent: Page/Page column 57.
[8]Patent: WO2009/150093,2009,A1 .Location in patent: Page/Page column 37-38.
[9]Patent: WO2009/150094,2009,A1 .Location in patent: Page/Page column 37-38.

3
[ 14922-91-9 ]
[ 1033760-94-9 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred mixture of <strong>[14922-91-9]5-bromo-2-ethylaniline</strong> (3.39 g, 200 mmol) in distilled water (110 ml) is added concentrated sulfuric acid (5.60 ml), followed by brief heating at reflux until dissolution. The mixture is allowed to cool to room temperature, producing a fine precipitate, then further cooled to approximately 0 0C in an ice/salt bath. To this slurry is added an aqueous solution of sodium nitrite (1.17 g, 16.94 mmol) in distilled water (10 ml) dropwise over 15 minutes, maintaining a temperature below 5 0C, followed by additional stirring for 30 minutes. The reaction mixture is next filtered then added to a second solution of aqueous potassium iodide (8.44 g, 50.83 mmol) in distilled water (45 ml) dropwise at room temperature. After the addition is complete the solution is briefly heated to 80 0C then allowed to cool to room temperature again. The reaction mixture is extracted with ethyl acetate (3 x 50 ml), and the organic phase is washed with 1 M aqueous hydrochloric acid (30 ml) and aqueous sodium thiosulfate (2 x 30 ml). After drying over anhydrous magnesium sulfate and concentration in vacuo 4-bromo-1-ethyl-2-iodobenzene (4.90 g) is furnished as an orange liquid.
		Step 2: Preparation of 4-bromo-1-ethyl-2-iodobenzeneTo a stirred mixture of <strong>[14922-91-9]5-bromo-2-ethylaniline</strong> (3.39 g, 200 mmol) in distilled water (110 ml) is added concentrated sulfuric acid (5.60 ml), followed by brief heating at reflux until dissolution. The mixture is allowed to cool to room temperature, producing a fine precipitate, then further cooled to approximately 0 0C in an ice/salt bath. To this slurry is added an aqueous solution of sodium nitrite (1.17 g, 16.94 mmol) in distilled water (10 ml) dropwise over 15 minutes, maintaining a temperature below 5 0C, followed by additional stirring for 30 minutes. The reaction mixture is next filtered then added to a second solution of aqueous potassium iodide (8.44 g, 50.83 mmol) in distilled water (45 ml) dropwise at room temperature. After the addition is complete the solution is briefly heated to 80 0C then allowed to cool to room temperature again. The reaction mixture is extracted with ethyl acetate (3 x 50 ml), and the organic phase is washed with 1 M aqueous hydrochloric acid (30 ml) and aqueous sodium thiosulfate (2 x 30 ml). After drying over anhydrous magnesium sulfate and concentration in vacuo 4-bromo-1-ethyl-2- iodobenzene (4.90 g) is furnished as an orange liquid.
		Step 2: Preparation of 4-bromo-1-ethyl-2-iodobenzeneTo a stirred mixture of <strong>[14922-91-9]5-bromo-2-ethylaniline</strong> (3.39 g, 200 mmol) in distilled water (110 ml) is added concentrated sulfuric acid (5.60 ml), followed by brief heating at reflux until dissolution. The mixture is allowed to cool to room temperature, producing a fine precipitate, then further cooled to approximately 0 C. in an ice/salt bath. To this slurry is added an aqueous solution of sodium nitrite (1.17 g, 16.94 mmol) in distilled water (10 ml) dropwise over 15 minutes, maintaining a temperature below 5 C., followed by additional stirring for 30 minutes. The reaction mixture is next filtered then added to a second solution of aqueous potassium iodide (8.44 g, 50.83 mmol) in distilled water (45 ml) dropwise at room temperature. After the addition is complete the solution is briefly heated to 80 C. then allowed to cool to room temperature again. The reaction mixture is extracted with ethyl acetate (3×50 ml), and the organic phase is washed with 1M aqueous hydrochloric acid (30 ml) and aqueous sodium thiosulfate (2×30 ml). After drying over anhydrous magnesium sulfate and concentration in vacuo 4-bromo-1-ethyl-2-iodobenzene (4.90 g) is furnished as an orange liquid.

		Step 2: Preparation of 4-bromo-1-ethyl-2-iodobenzene <n="59"/>To a stirred mixture of <strong>[14922-91-9]5-bromo-2-ethylaniline</strong> (3.39 g, 200 mmol) in distilled water (110 ml) is added concentrated sulfuric acid (5.60 ml), followed by brief heating at reflux until dissolution. The mixture is allowed to cool to room temperature, producing a fine precipitate, then further cooled to approximately 0 0C in an ice/salt bath. To this slurry is added an aqueous solution of sodium nitrite (1.17 g, 16.94 mmol) in distilled water (10 ml) dropwise over 15 minutes, maintaining a temperature below 5 0C, followed by additional stirring for 30 minutes. The reaction mixture is next filtered then added to a second solution of aqueous potassium iodide (8.44 g, 50.83 mmol) in distilled water (45 ml) dropwise at room temperature. After the addition is complete the solution is briefly heated to 80 0C then allowed to cool to room temperature again. The reaction mixture is extracted with ethyl acetate (3 x 50 ml), and the organic phase is washed with 1M aqueous hydrochloric acid (30 ml) and aqueous sodium thiosulfate (2 x 30 ml). After drying over anhydrous magnesium sulfate and concentration in vacuo 4-bromo-1-ethyl-2- iodobenzene (4.90 g) is furnished as an orange liquid.
		To a stirred mixture of <strong>[14922-91-9]5-bromo-2-ethylaniline</strong> (3.39 g, 200 mmol) in distilled water (1 10 ml) is added concentrated sulfuric acid (5.60 ml), followed by brief heating at reflux until dissolution. The mixture is allowed to cool to room temperature, producing a fine precipitate, then further cooled to approximately 0 0C in an ice/salt bath. To this slurry is added an aqueous solution of sodium nitrite (1.17 g, 16.94 mmol) in distilled water (10 ml) dropwise over 15 minutes, maintaining a temperature below 5 0C, followed by additional stirring for 30 minutes. The reaction mixture is next filtered then added to a second solution of aqueous potassium iodide (8.44 g, 50.83 mmol) in distilled water (45 ml) dropwise at room temperature. After the addition is complete the solution is briefly heated to 80 0C then allowed to cool to room temperature again. The reaction mixture is extracted with ethyl acetate (3 x 50 ml), and the organic phase is washed with 1 M aqueous hydrochloric acid (30 ml) and aqueous sodium thiosulfate (2 x 30 ml). After drying over anhydrous magnesium sulfate and concentration in vacuo 4-bromo-1-ethyl-2-iodobenzene (4.90 g) is furnished as an orange liquid.
		To a stirred mixture of <strong>[14922-91-9]5-bromo-2-ethylaniline</strong> (3.39 g, 200 mmol) in distilled water (110 ml) is added concentrated sulfuric acid (5.60 ml), followed by brief heating at reflux until dissolution. The mixture is allowed to cool to room temperature, producing a fine precipitate, then further cooled to approximately 0 0C in an ice/salt bath. To this slurry is added an aqueous solution of sodium nitrite (1.17 g, 16.94 mmol) in distilled water (10 ml) dropwise over 15 minutes, maintaining a temperature below 5 0C, followed by additional stirring for 30 minutes. The reaction mixture is next filtered then added to a second solution of aqueous potassium iodide (8.44 g, 50.83 mmol) in distilled water (45 ml) dropwise at room temperature. After the addition is complete the solution is briefly heated to 80 0C then allowed to cool to room temperature again. The reaction mixture is extracted with ethyl acetate (3 x 50 ml), and the organic phase is washed with 1 M aqueous hydrochloric acid (30 ml) and aqueous sodium thiosulfate (2 x 30 ml). After drying over anhydrous magnesium sulfate and concentration in vacuo 4-bromo-1-ethyl-2-iodobenzene (4.90 g) is furnished as an orange liquid.

References: [1]Patent: WO2008/71405,2008,A1 .Location in patent: Page/Page column 63.
[2]Patent: WO2011/6543,2011,A1 .Location in patent: Page/Page column 49.
[3]Patent: US2012/190545,2012,A1 .Location in patent: Page/Page column 23.
[4]Patent: WO2008/145336,2008,A1 .Location in patent: Page/Page column 57-58.
[5]Patent: WO2009/150093,2009,A1 .Location in patent: Page/Page column 38.
[6]Patent: WO2009/150094,2009,A1 .Location in patent: Page/Page column 38.

4
[ 14922-91-9 ]
[ 1679-18-1 ]
[ 1033760-80-3 ]

Yield	Reaction Conditions	Operation in experiment
		Step 44-Chlorophenylboronic acid (13.2 g, 0.08 mol) and tetrakis(triphenylphosphine) palladium (0) (2.4 g, 0.002 mol) are added to a solution of <strong>[14922-91-9]5-bromo-2-ethylaniline</strong> (14.1 g, 0.07 mol) in 1 ,2- dimethoxyethane (140 ml). After stirring the reaction mixture for 15 minutes at 2O0C, a solution of 20% aqueous sodium carbonate (300ml) is added to the mixture, and the resulting mixture is refluxed for 24 hours. The reaction mixture is cooled to room temperature, diluted with water and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with 5% ethyl acetate in hexane to give 5-(4-chlorophenyl)- 2-ethylaniline (14.3 g).
		4-Chlorophenylboronic acid (13.2 g, 0.08 mol) and tetrakis(triphenylphosphine) palladium (0) (2.4 g, 0.002 mol) are added to a solution of <strong>[14922-91-9]5-bromo-2-ethylaniline</strong> (14.1 g, 0.07 mol) in 1 ,2- dimethoxyethane (140 ml). After stirring the reaction mixture for 15 minutes at 2O0C, a solution of <n="73"/>20% aqueous sodium carbonate (300ml) is added to the mixture, and the resulting mixture is refluxed for 24 hours. The reaction mixture is cooled to room temperature, diluted with water and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with 5% ethyl acetate in hexane to give 5-(4-chlorophenyl)- 2-ethylaniline (14.3 g).
		Step 44-Chlorophenylboronic acid (13.2 g, 0.08 mol) and tetrakis(triphenylphosphine) palladium (0) (2.4 g, 0.002 mol) are added to a solution of <strong>[14922-91-9]5-bromo-2-ethylaniline</strong> (14.1 g, 0.07 mol) in 1 ,2- dimethoxyethane (140 ml). After stirring the reaction mixture for 15 minutes at 20C, a solution of 20% aqueous sodium carbonate (300ml) is added to the mixture, and the resulting mixture is refluxed for 24 hours. The reaction mixture is cooled to room temperature, diluted with water and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with 5% ethyl acetate in hexane to give 5-(4-chlorophenyl)- 2-ethylaniline (14.3 g).

References: [1]Patent: WO2010/46194,2010,A1 .Location in patent: Page/Page column 66.
[2]Patent: WO2008/110307,2008,A1 .Location in patent: Page/Page column 71-72.
[3]Patent: WO2008/110308,2008,A2 .Location in patent: Page/Page column 169.

5
[ 589-16-2 ]
[ 14922-91-9 ]

References: [1]Patent: US2012/190545,2012,A1 .
[2]Patent: WO2008/110307,2008,A1 .
[3]Patent: WO2008/110308,2008,A2 .
[4]Patent: WO2008/145336,2008,A1 .
[5]Patent: WO2011/6543,2011,A1 .

6
[ 51529-96-5 ]
[ 14922-91-9 ]

References: [1]Patent: US2012/190545,2012,A1 .
[2]Patent: WO2008/110307,2008,A1 .
[3]Patent: WO2008/145336,2008,A1 .
[4]Patent: WO2011/6543,2011,A1 .

7
[ 14922-91-9 ]
[ 1033760-95-0 ]

References: [1]Patent: US2012/190545,2012,A1 .
[2]Patent: WO2008/145336,2008,A1 .
[3]Patent: WO2009/150093,2009,A1 .
[4]Patent: WO2009/150094,2009,A1 .
[5]Patent: WO2011/6543,2011,A1 .

8
[ 14922-91-9 ]
[ 1033760-96-1 ]

References: [1]Patent: US2012/190545,2012,A1 .
[2]Patent: WO2008/145336,2008,A1 .
[3]Patent: WO2009/150093,2009,A1 .
[4]Patent: WO2009/150094,2009,A1 .
[5]Patent: WO2011/6543,2011,A1 .

9
[ 14922-91-9 ]
2-(4'-chloro-4-ethyl-2'-methylbiphenyl-3-yl)-4,4-dimethyl-cyclohexane-1,3-dione [ No CAS ]

References: [1]Patent: US2012/190545,2012,A1 .
[2]Patent: WO2011/6543,2011,A1 .

10
[ 14922-91-9 ]
2-(5-bromo-2-ethylphenyl)-4,4-dimethylcyclohexane-1,3-dione [ No CAS ]

References: [1]Patent: US2012/190545,2012,A1 .
[2]Patent: WO2011/6543,2011,A1 .

11
[ 14922-91-9 ]
[ 1033760-81-4 ]

References: [1]Patent: WO2008/110307,2008,A1 .

12
[ 14922-91-9 ]
[ 1033760-82-5 ]

References: [1]Patent: WO2008/110307,2008,A1 .
[2]Patent: WO2008/110308,2008,A2 .

13
[ 14922-91-9 ]
[ 1068111-07-8 ]

References: [1]Patent: WO2008/110308,2008,A2 .

14
[ 14922-91-9 ]
C₁₇H₁₇BrO₂ [ No CAS ]