Triphenylphosphine → 1-(3-Bromopropyl)-3-(trifluoromethyl)benzene

HRID 1093327

반응식

HRID 1093327 반응식
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11]O)[CH:6]=[CH:7][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>C(Cl)Cl>[Br:34][CH2:11][CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 18755618Benzenepropanol, 3-(trifluoromethyl)-

생성물 1

HCID 197833671-(3-Bromopropyl)-3-(trifluoromethyl)benzene수율 73%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Compound 12-1 (9.00 g) was dissolved in methylene chloride (80 ml), triphenylphosphine (12.8 g) and N-bromosuccinimide (8.63 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 1 hr, and further at room temperature for 3 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (200 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone) to give the object product (8.59 g) as a colorless oil.

후처리

  1. temperaturecooling
  2. temperaturecooling for 1 hr
  3. washThe reaction mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionDiethyl ether (200 ml) was added
  7. filtrationthe precipitated triphenylphosphine oxide was filtered off
  8. concentrationThe concentrate of the filtrate
  9. customwas purified by silica gel column chromatography (hexane alone)

출처 및 근거

ORD 기록
ord-fafba66b78fb4d6eb5e86fedb171f8d3
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129361B2

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