Dimethyl Sulfoxide → 1-(2,2-Diphenylvinyl)-3,5-dibromobenzene

HRID 1827616노트

반응식

HRID 1827616 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[CH:5]=O.[C:11]1([CH:17](P(=O)(OCC)OCC)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CS(C)=O.CC(C)([O-])C.[K+]>O>[C:11]1([C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:5][C:4]2[CH:3]=[C:2]([Br:1])[CH:9]=[C:8]([Br:10])[CH:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 6220773,5-DibromobenzaldehydeHCID 10267017Diethyl benzhydrylphosphonateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 221380311-(2,2-Diphenylvinyl)-3,5-dibromobenzene수율 74%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Under an atmosphere of argon, 3,5-dibromobenzaldehyde (12.1 g, 46 L mmole) and diethyl diphenylmethylphosphonate (15 g, 49 mmole, 1.1 eq) were dissolved into dimethyl sulfoxide (DMSO) (60 ml). To the resultant solution, potassium t-butoxide (6.2 g, 55 mmole, 1.2 eq) was added in small portions and the obtained solution was stirred at the room temperature for 9 hours and left standing for one night. After water (60 ml) was added, the reaction mixture was subjected to extraction with ethyl acetate (250 ml). The obtained organic layer was washed with water (100 ml) and a saturated aqueous solution of sodium chloride (50 ml) and dried with magnesium sulfate. Then, the solvent was removed by distillation and a deep brown oil was obtained. The obtained oil was purified by the column chromatography (silica gel/hexane and hexane+3% dichloromethane, successively) and a white solid (14.0 g, 74%) was obtained.

후처리

  1. waitleft
  2. waitstanding for one night
  3. extractionthe reaction mixture was subjected to extraction with ethyl acetate (250 ml)
  4. washThe obtained organic layer was washed with water (100 ml)
  5. dry with materiala saturated aqueous solution of sodium chloride (50 ml) and dried with magnesium sulfate
  6. customThen, the solvent was removed by distillation
  7. customa deep brown oil was obtained
  8. customThe obtained oil was purified by the column chromatography (silica gel/hexane and hexane+3% dichloromethane

출처 및 근거

ORD 기록
ord-232dca43865243219f645aef89b90032
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053255B2

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