Dimethyl Sulfoxide → 1,1-Diphenyl-4-bromobutane

HRID 963979

반응식

HRID 963979 반응식
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:9][CH2:10]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CS(C)=O>CCOCC>[Br:19][CH2:10][CH2:9][CH2:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 925194,4-Diphenylbutan-1-ol

생성물 1

HCID 122234581,1-Diphenyl-4-bromobutane수율 72.4%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

4,4-Diphenyl-1-butanol (22.41 g, 0.099 mol) was dissolved in ether (250 mL). CBr4 (41.07 g, 0.123 mol) was added and the reaction cooled to 0° C. Triphenylphosphine (38.96 g, 0.148 mol) in ether (400 mL) was added dropwise to the reaction. The reaction was then allowed to warm to room temperature overnight. DMSO (3.51 mL) was added, and the reaction allowed to stir for 8 hours. The white precipitate was filtered and washed with ether (100 mL). The ether was removed in vacuo, and the residue washed with hexanes and filter. The hexanes were removed in vacuo, and the residue chromatographed on silica gel eluting with hexanes to give 20.72 g (72%) of desired product as an oil.

후처리

  1. temperatureto warm to room temperature overnight
  2. filtrationThe white precipitate was filtered
  3. washwashed with ether (100 mL)
  4. customThe ether was removed in vacuo
  5. washthe residue washed with hexanes
  6. filtrationfilter
  7. customThe hexanes were removed in vacuo
  8. customthe residue chromatographed on silica gel eluting with hexanes

출처 및 근거

ORD 기록
ord-15294c53c5684764a7b2f8ffc4894105
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05767129

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