Carbon Dioxide → 4-Bromo-2,5-difluorobenzoic acid

HRID 523233

반응식

HRID 523233 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([Br:9])=[CH:4][C:3]=1[F:10].C([Li])CCC.[C:16](=[O:18])=[O:17]>C(OCC)C>[Br:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([C:16]([OH:18])=[O:17])=[C:3]([F:10])[CH:4]=1

참가 물질

5

반응물 3

HCID 280Carbon DioxideHCID 675961,4-Dibromo-2,5-difluorobenzeneHCID 178418339Butyllithium

생성물 1

HCID 8228574-Bromo-2,5-difluorobenzoic acid수율 53%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-78 °C

실험 절차

A solution of 1,4-dibromo-2,5-difluorobenzene (640 mg, 2.35 mmol) in dry diethyl ether (10 mL) cooled in a dry ice-acetone bath was treated dropwise with 2.5 M n-butyllithium in hexanes (1.04 mL, 2.59 mmol). The solution was stirred at −78° C. for 30 min, then was treated with a piece of dry ice. The cooling bath was removed after 5 min and the mixture was stirred for another 30 min while warming to room temperature. The mixture was diluted with EtOAc and water. The organic phase was separated and washed twice with saturated aqueous NaHCO3. The combined aqueous phases were acidified with 1M aqueous HCl, extracted twice with DCM, and the combined organic phases were dried and concentrated to give 4-bromo-2,5-difluorobenzoic acid as a white solid (297 mg, 53% yield).

후처리

  1. customThe cooling bath was removed after 5 min
  2. stirringthe mixture was stirred for another 30 min
  3. temperaturewhile warming to room temperature
  4. additionThe mixture was diluted with EtOAc and water
  5. customThe organic phase was separated
  6. washwashed twice with saturated aqueous NaHCO3
  7. extractionextracted twice with DCM
  8. customthe combined organic phases were dried
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5e76969404fd4db6871fcd7917306608
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334290B2

연결된 노트

불러오는 중…