تفاعل #48345

معادلة التفاعل

3-Chloro-2,4-difluorobenzoic acid

Borane methylsulfide

Na2CO3

→

title compound

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

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe solution was cooled to 0 deg
2. 2
   درجة الحرارةThe solution was cooled in an ice bath
3. 3
   تركيزThe material was concentrated on the rotovap to a white solid
4. 4
   workup.ADDITIONdiluted with dichloromethane (50 mL)
5. 5
   ترشيحthe mixture was filtered through Celite
6. 6
   أخرىThe layers were separated
7. 7
   تجفيفthe organic layer was dried over sodium sulfate
8. 8
   تركيزconcentrated
9. 9
   أخرىThe residue was purified through silica gel (500 mL)

الإجراء التجريبي

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.

المصدر