2'-Bromoacetophenone → 1-(2-Bromophenyl)ethanol

To a solution of 2′-bromoacetophenone (15 g, 74.6 mmol) in 150 ml MeOH under argon at room temperature was added NaBH4 (4.23 g, 0.11 mol). The reaction mixture was stirred at room temperature for 24 h then quenched by addition of water. HCl 5 N was added until pH 6-7. MeOH was evaporated. The residue was dissolved in ether and washed once with water, once with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel (eluent: heptane: ethylacetate 1:1) to yield 14.8 g (99%) of (RS)-1-(2-bromo-phenyl)-ethanol as a colorless oil.

1. customthen quenched by addition of water. HCl 5 N
2. additionwas added until pH 6-7
3. customMeOH was evaporated
4. dissolutionThe residue was dissolved in ether
5. washwashed once with water, once with brine
6. dry with materialThe organic phase was dried over Na2SO4
7. concentrationconcentrated in vacuo
8. customThe residue was chromatographed on silica gel (eluent: heptane: ethylacetate 1:1)

ORD record

ord-5827c30ac5f64dc4b3dfde3a6a4f2c04

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08664216B2