Ethyl Acetate → 2-(4-Bromophenyl)propan-2-ol

A solution of methyl p-bromobenzoate (3 g, 13.2 mmol) in tetrahydrofuran (14 mL) cooled to −30° C. was treated dropwise with methyl magnesium bromide (1 M in diethyl ether, 105.5 mmol, 105.5 mL). Upon completion of addition, the resulting suspension was allowed to warm to room temperature and was stirred for 5 hours. Saturated aqueous ammonium chloride (100 mL) was added slowly and the mixture was diluted with ethyl acetate (100 mL). The organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over magnesium sulfate, were filtered, and the solvent was removed in vacuo. Purification by silica gel chromatography (10:1 hexanes—ethyl acetate) gave 2.2 g (79% yield) of 2-(4-bromo-phenyl)-propan-2-ol. 13C NMR (100 MHz, CDCl3) d 148.4, 131.4, 126.6, 120.8, 72.5, 31.9; MS (AP/Cl) 197.1, 199.1 (M+H)+.

1. additionUpon completion of addition
2. customThe organic and aqueous layers were separated
3. extractionthe aqueous layer was extracted with ethyl acetate (3×50 mL)
4. dry with materialThe combined organic layers were dried over magnesium sulfate
5. filtrationwere filtered
6. customthe solvent was removed in vacuo
7. customPurification by silica gel chromatography (10:1 hexanes—ethyl acetate)

ORD record

ord-dfcaea20d0194f63b5083a1976c1f16f

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07479559B2