ChemicalBook CAS DataBase List 2-Bromo-3′-hydroxyacetophenone

2-Bromo-3′-hydroxyacetophenone synthesis

6synthesis methods

Product Name:2-Bromo-3′-hydroxyacetophenone
CAS Number:2491-37-4
Molecular formula:C8H7BrO2
Molecular Weight:215.04

5000-65-7 Synthesis

5000-65-7
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2491-37-4
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$29.00/1g

Yield: 24%

Reaction Conditions:

Stage #1:2-bromo-3'-methoxyacetophenone with boron tribromide in dichloromethane at -10; for 1.5 h;
Stage #2: with water in dichloromethane at 0;

Steps:

95
To a stirred solution of 2-bromo-1-(3-methoxy-phenyl)-ethanone (Aldrich, 3.44 g, 15 mmol) in methylene chloride (20 mL) at -10° C., boron tribromide (Aldrich, 16.5 mmol, 1M solution in CH2Cl2, 16.5 mL) was added slowly and the mixture was stirred for 1.5 hours. The reaction was quenched with ice water and the organic layer was separated. The aqueous layer was extracted with EtOAc and the extracts were combined and dried with sodium sulfate. Removal of solvent gave a greenish solid which was purified by chromatography (EtOAc/Hexane, 25%) gave an off-white solid. 770 mg, 24%. The compound was used directly for the next step.

References:

Ding, Qingjie;Jiang, Nan;Kim, Kyungjin;Lovey, Allen John;McComas, Warren William US2005/239843, 2005, A1 Location in patent:Page/Page column 55