反应 #1269906

ord-5827c30ac5f64dc4b3dfde3a6a4f2c04

反应方程式

CC(=O)c1ccccc1Br
2′-bromoacetophenone
[BH4-].[Na+]
NaBH4
CC(O)c1ccccc1Br
(RS)-1-(2-bromo-phenyl)-ethanol
收率 99.0%

试剂

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他then quenched by addition of water. HCl 5 N
  2. 2
    workup.ADDITIONwas added until pH 6-7
  3. 3
    其他MeOH was evaporated
  4. 4
    workup.DISSOLUTIONThe residue was dissolved in ether
  5. 5
    洗涤washed once with water, once with brine
  6. 6
    干燥The organic phase was dried over Na2SO4
  7. 7
    浓缩concentrated in vacuo
  8. 8
    其他The residue was chromatographed on silica gel (eluent: heptane: ethylacetate 1:1)

实验过程

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.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08664216B2uspto-grants-2014_03