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

HRID 1584101노트

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HRID 1584101 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

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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-e47de7e057e442608b92dbdeb688a01b
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05932573

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