Diisobutylaluminum hydride → 4-(Bromomethyl)benzyl alcohol

To a solution of 4-bromomethyl-benzoic acid methyl ester (5 g, 21.82 mmol) in DCM (200 mL) is added DIBAL-H (1.0 M in hexane, 54.56 mL, 54.56 mmol) drop wise at −78° C. The reaction mixture is allowed to warm to room temperature and stirred for 16 hours. The reaction mixture is quenched with sodium potassium tartrate (10% solution, 8 mL) and diluted with DCM (100 mL). The combined organic layer is washed with water (50 mL), brine (25 mL), dried over sodium sulfate, and evaporated to give the title compound as an off white solid (3.5 g, 81%). 1H NMR (400 MHz, CDCl3) δ 7.23-7.21 (m, 2H), 7.4-7.3 (m, 2H), 4.5-4.3 (bs, 2H), 4.68 (s, 2H).

1. customThe reaction mixture is quenched with sodium potassium tartrate (10% solution, 8 mL)
2. additiondiluted with DCM (100 mL)
3. washThe combined organic layer is washed with water (50 mL), brine (25 mL)
4. dry with materialdried over sodium sulfate
5. customevaporated

ORD record

ord-767c23fb00424eebbe3ae3a32c488198

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383642B2