Sodium borohydride → 1-(3-Bromophenyl)-4-fluorobutan-1-ol

Temperature

0 °C

A solution of 0.3 gm (1.22 mmol) of 1-(3-bromo-phenyl)-4-fluorobutan-1-one in THF at 0° C. was treated with 0.055 gm (1.47 mmol) of solid NaBH4, stirred at 0° C. for 0.5 h, allowed to warm to room temperature, stirred for 18 h, quenched with aqueous NH4Cl and poured into EtOAC. The phases were separated. The organic phase was washed sequentially with water and brine, dried over Na2SO4 and concentrated under reduced pressure to give 1-(3-bromophenyl)-4-fluorobutan-1-ol as an oil, 0.29 gm (96% yield) of an oil. This oil was dissolved in CH2Cl2, cooled to 0° C., treated with 0.23 mL (1.75 mmol) of DAST, stirred at 0° C. for 0.5 h, allowed to warm to room temperature, and stirred at room temperature for 18 h, quenched with water and poured into EtOAc. The phases were separated. The organic phase was washed sequentially with water and brine, dried over Na2SO4 and carefully concentrated at reduced pressure. The concentrate was used without further purification in Step e.

1. temperatureto warm to room temperature
2. stirringstirred for 18 h
3. customquenched with aqueous NH4Cl
4. additionpoured into EtOAC
5. customThe phases were separated
6. washThe organic phase was washed sequentially with water and brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under reduced pressure

ORD record

ord-2f01aa1463f142c1bc02b987d38f7cd8

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07423158B2