反応 #48345

反応方程式

3-Chloro-2,4-difluorobenzoic acid

Borane methylsulfide

Na2CO3

→

title compound

(3-Chloro-2,4-difluorophenyl)methanol

溶媒

THF

反応条件

後処理

1. 1
   温度the solution was cooled to 0 deg
2. 2
   温度The solution was cooled in an ice bath
3. 3
   濃縮The material was concentrated on the rotovap to a white solid
4. 4
   workup.ADDITIONdiluted with dichloromethane (50 mL)
5. 5
   ろ過the mixture was filtered through Celite
6. 6
   その他The layers were separated
7. 7
   乾燥the organic layer was dried over sodium sulfate
8. 8
   濃縮concentrated
9. 9
   その他The residue was purified through silica gel (500 mL)

実験手順

3-Chloro-2,4-difluorobenzoic acid (5.37 g, 27.9 mmol) was dissolved in THF (20 mL) and the solution was cooled to 0 deg. Borane methylsulfide (2.0 M in THF, 55.8 ml, 112 mmol) was added. The resulting solution was warmed to rt and stirred for 14 h. The solution was cooled in an ice bath, and 10% aqueous Na2CO3 (7 mL) was added slowly. The material was concentrated on the rotovap to a white solid. The residue was acidified with 3M aqueous HCl (30 mL), diluted with dichloromethane (50 mL), and the mixture was filtered through Celite. The layers were separated, and the organic layer was dried over sodium sulfate and concentrated. The residue was purified through silica gel (500 mL) using 30% EtOAc-hexane, to afford the title compound.

出典