79636-93-4|4-Bromo-1-ethoxy-2-methylbenzene| Ambeed

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Quality Control of [ 79636-93-4 ] Purity: 98% SDS Specification

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Product Details of [ 79636-93-4 ]

CAS No. :	79636-93-4
Formula :	C₉H₁₁BrO
M.W :	215.09
SMILES Code :	CC1=CC(Br)=CC=C1OCC
MDL No. :	MFCD12547896
InChI Key :	VLEKYZFNWIUBGE-UHFFFAOYSA-N
Pubchem ID :	12677366

Safety of [ 79636-93-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317-H319
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 79636-93-4 ]

* 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 [ 79636-93-4 ]

[ 79636-93-4 ] Synthesis Path-Downstream 1~20

1
[ 79636-93-4 ]
[ 79636-94-5 ]

References: [1]Tetrahedron Letters,1981,vol. 22,p. 2605 - 2608.

3
[ 2362-12-1 ]
[ 75-03-6 ]
[ 79636-93-4 ]

Yield	Reaction Conditions	Operation in experiment
81%		To a solution of 3-bromocresol (7.0 g, 37.4 mmol, 1.0 eq) in 20 mL of dry dimethylsulfoxide, anhydrous potassium carbonate was added (10.3 g, 74.8 mmol, 2.0 eq.) and the mixture was stirred for 20 min at room temperature. After this time, ethyliodide (8.6 g, 44.9 mmol, 1.2 eq.) was added and the resulting mixture was further stirred for 16 hours at 60 C. The reaction mixture was examined LC-MS which showed >90% conversion to the desired product. The reaction mixture was cooled to room temperature, 100 mL of water was added and the mixture was extracted with dichloromethane. The organic fraction was dried over sodium sulfate and the crude product was purified by flash chromatography eluting with cyclohexane. 7.8 g of clean product was obtained as colorless liquid (yield: 81%)Mass (calculated) C9H11BrO [215] Not observedLC Rt=2.70 min (5 min method) 98%1H-NMR (CDCl3): 1.40 (t, 3H), 2.18 (s, 3H), 4.00 (q, 2H), 6.66 (d, 1H), 7.21 (m, 1H), 7.24 (m, 1H).
	With caesium carbonate; In N,N-dimethyl-formamide; for 12.0h;	To a solution of 4-bromo-2-methylphenol (5.0 g, 26.7 mmol) in DMF (20 mL) was added cesium carbonate (13.0 g, 39.9 mmol) and iodoethane (2.6 mL, 32.5 mmol) and the suspension stirred vigorously for 12 hrs. The resulting mixture was partitioned between EtOAc and water. The organic phase was then separated, washed further with water, dried (MgSO i), and filtered. Evaporation of the filtrate in vacuo afforded 4-bromo-l-ethoxy-2-methylbenzene which could be used without further purification.
	With caesium carbonate; In N,N-dimethyl-formamide; for 24.0h;	Step 1: To a solution of 4-bromo-2-methylphenol (5.0 g, 26.7 mmol) in DMF (20 mL) was added CS2CO3 (13.0 g, 39.9 mmol) and iodoethane (2.6 mL, 32.5 mmol). The reaction was stirred vigorously for 24 hrs after which the suspension was partitioned between EtOAc and water, the organic phase extracted, wash with water, dried (MgSO i), filtered and evaporated to afford 4-bromo-l -ethoxy-2-methylbenzene used without further purification.

References: [1]Patent: US2009/209529,2009,A1 .Location in patent: Page/Page column 17.
[2]Patent: WO2013/134562,2013,A1 .Location in patent: Paragraph 00122.
[3]Patent: WO2014/99503,2014,A1 .Location in patent: Paragraph 00123.

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[ 79636-93-4 ]
[ 2142-63-4 ]
[ 1180015-53-5 ]

Yield	Reaction Conditions	Operation in experiment
		4-[1-(3-Bromo-phenyl)-vinyl]-1-ethoxy-2-methyl-benzene To a suspension of magnesium turnings (963 mg, 39.6 mmol, 1.2 eq) in 5 mL of dry tetrahydrofuran, 0.1 mL of 1,2-dibromoethane were added followed by 5 mL of a tetrahydrofuran solution of 4-bromo-1-ethoxy-2-methyl-benzene (7.8 g, 36.3 mmol, 1.1 eq in 25 mL tetrahydrofuran). The resulting mixture was gently heated to initiate the reaction. The remaining solution of bromide was added dropwise at such a rate that the reaction could reflux without external heating. After the addition the reaction mixture was heated at reflux for further 2 hours. The mixture was cooled to 0 C. and a solution of 3-bromoacetophenone (6.56 g, 33.0 mmol, 1.0 eq) in tetrahydrofuran (30 mL) was added dropwise. After 2 hours LCMS showed complete conversion to the desired product. 50 mL of water were added followed by 35 mL of 1M aqueous HCl. The organic fraction was washed with brine, dried over sodium sulfate and concentrated to give a yellow oil. The oil was dissolved in 10 mL of acetic acid. 0.3 mL of 98% sulfuric acid were added and the dark solution was stirred at room temperature. After 30 min LCMS showed complete conversion to the desired product. Crushed ice was added to the reaction mixture which was then extracted with dichloromethane. The organic fraction was collected, washed with water, saturated sodium bicarbonate solution and dried with over sodium sulfate. The crude product was purified by flash chromatography eluding with cyclohexane. 7.5 g of clean product was obtained as colorless liquid (yield: 63%) Mass (calculated) C17H17BrO [317]; (found) [M+H+]=318 LC Rt=1.97 min (5 min method) 93% TLC Rf=0.8 (cyclohexane/ethyl acetate 80:20)

References: [1]Patent: US2009/209529,2009,A1 .Location in patent: Page/Page column 18.

5
[ 79636-93-4 ]
[ 1314711-29-9 ]

References: [1]Patent: WO2013/134562,2013,A1 .
[2]Patent: WO2014/99503,2014,A1 .

6
[ 79636-93-4 ]
[ 1094438-61-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 3.0h;Reflux;	To the previously synthesized ether (4.97 g, 23.1 mmol) in carbon tetrachloride (80 mL) was added N-bromosuccinimide (4.93 g, 27.6 mmol) and benzoyl peroxide (100 mg). The resulting solution was heated to reflux for 3 hrs, allowed to cool, partially evaporated and then filtered. The filtrate was evaporated in vacuo to afford 4-bromo-2-(bromomethyl)-l-ethoxybenzene which could be used without further purification.
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 3.0h;Reflux;	Step 2: To a solution of <strong>[79636-93-4]4-bromo-1-ethoxy-2-methylbenzene</strong> (5.0 g, 23.1 mmol) in CCI4 (80 mL) was added N-bromosuccinimide (4.93 g, 27.6 mmol) and benzoyl peroxide (100 mg, cat.). The reaction mixture was then heated to reflux for a period of 3 hrs after which it was allowed to cool, partially evaporated then filtered to remove the succinimide. The filtrate was then evaporated to dryness to afford the benzylbromide which was used without further purification

References: [1]Patent: WO2013/134562,2013,A1 .Location in patent: Paragraph 00123.
[2]Patent: WO2014/99503,2014,A1 .Location in patent: Paragraph 00124.
[3]Journal of Medicinal Chemistry,2020,vol. 63,p. 4528 - 4554.

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[ 79636-93-4 ]
[ 7062-41-1 ]

References: [1]Patent: WO2013/134562,2013,A1 .
[2]Patent: WO2014/99503,2014,A1 .

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[ 79636-93-4 ]
[ 1616372-40-7 ]

References: [1]Patent: WO2014/99503,2014,A1 .

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C₃₆H₄₂N₄O₂ [ No CAS ]

References: [1]Patent: WO2014/99503,2014,A1 .

10
[ 79636-93-4 ]
[ 107-21-1 ]
[ 1310403-97-4 ]

References: [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 60 - 66.

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[ 79636-93-4 ]
[ 1385022-69-4 ]

References: [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 60 - 66.
[2]European Journal of Organic Chemistry,2015,vol. 2015,p. 60 - 66.

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[ 79636-93-4 ]
[ 1385022-73-0 ]

References: [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 60 - 66.

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[ 79636-93-4 ]
[ 1385022-77-4 ]

References: [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 60 - 66.

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[ 79636-93-4 ]
[ 1385022-71-8 ]

References: [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 60 - 66.

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[ 79636-93-4 ]
tert-butyl (5-bromo-2-ethoxybenzyl)carbamate [ No CAS ]