Carbon tetrabromide → 1-(3-Bromo-1,1-difluoropropyl)-4-fluorobenzene

HRID 1925536노트

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HRID 1925536 반응식
Br[C:2]([Br:5])(Br)Br.[F:6][C:7]([F:18])([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[CH2:8]CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCCC.CC(=O)OCC>C(Cl)Cl.O>[Br:5][CH2:2][CH2:8][C:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)([F:6])[F:18]

참가 물질

7

반응물 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21226206Ethyl acetate hexaneHCID 671341563,3-Difluoro-3-(4-fluorophenyl)propan-1-ol

생성물 1

HCID 671338221-(3-Bromo-1,1-difluoropropyl)-4-fluorobenzene수율 94.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

3.1 g (9.5 mmol) of tetrabromomethane were added to a solution of 1.0 g (5.3 mmol) of 3,3-difluoro-3-(4-fluorophenyl)propan-1-ol in DCM (20 ml) and cooled to 0° C. At that temperature, 2.48 g (9.5 mmol) of triphenylphosphine were added in portions. Stirring was then carried out for 3 h at RT. The mixture was then diluted with water (50 ml) and extracted with EA (3×60 ml). The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 24:1) of the residue yielded 1.25 g (5.0 mmol, 94%) of 1-(3-bromo -1,1-difluoropropyl)-4-fluorobenzene.

후처리

  1. extractionextracted with EA (3×60 ml)
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d7e7f7cc6abf42dda0d2a48087415902
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178684B2

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