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

HRID 1827616ノート

反応式

HRID 1827616 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-232dca43865243219f645aef89b90032
出典データセット
uspto-grants-2006_05
特許番号
US07053255B2

反応ノート

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