Water → (4'-Bromobiphenyl-4-yl)acetone

HRID 1626789노트

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HRID 1626789 반응식
C[Li].C([O:5][CH2:6][CH3:7])C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21]C(N(OC)C)=O)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.O>O1CCCC1>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:6](=[O:5])[CH3:7])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 3283Diethyl EtherHCID 866700832-(4'-Bromobiphenyl-4-yl)-N-methoxy-N-methylacetamideHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 68193283(4'-Bromobiphenyl-4-yl)acetone수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of methyllithium in diethyl ether (40 mL, 44 mmol) was diluted with tetrahydrofuran (120 mL), and a solution of 2-(4′-bromobiphenyl-4-yl)-N-methoxy-N-methylacetamide (12 g, 37 mmol) in tetrahydrofuran (50 mL) was added at −78° C., followed by stirring at the same temperature for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate, and subsequently the solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.50 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (7.6 g, 26 mmol) as a white solid (yield 71%).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. distillationsubsequently the solvent was distilled off under reduced pressure
  3. customThe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  4. concentrationa fraction corresponding to the Rf value=0.50 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8ff3149660df468d9359fbab80b4db33
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785462B2

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