Water → HCID 21099420、化合物

HRID 2376971ノート

反応式

HRID 2376971 の反応式
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.[Na+].CN(C)CCN.O>CS(C)=O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])(=[O:19])=[O:18])=[CH:13][CH:12]=1

参加物

6

反応物 4

HCID 962WaterHCID 66053N,N-DimethylethylenediamineHCID 811292-BromobenzaldehydeHCID 23670685Sodium 4-bromobenzene-1-sulfinate

生成物 1

HCID 21099420HCID 21099420、化合物収率 55%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

2-Bromobenzaldehyde (1.55 g, 8.4 mmol), sodium 4-bromophenylsulfinate (2.79 g, 10 mmol) and copper(I) trifluoromethanesulfonate benzene complex (500 mg, 1 mmol) were combined in dimethylsulfoxide (10 mL) under nitrogen and degassed. The suspension was heated to 110° C. and N,N-dimethylethylenediamine (176 mg, 2 mmol) was added. The reaction was heated until the colour became clear and pale yellow, then cooled and poured into water. The products were extracted into ethyl acetate. The organic layer was washed with water:brine (1:1, ×5), dried over MgSO4 and evaporated in vacuo. The residue was triturated with isohexane to give 2-[(4-bromophenyl)sulfonyl]benzaldehyde (1.5 g, 55%). δH (400 MHz, CDCl3): 10.76 (1H, s), 8.14-8.12 (1H, m), 7.98-7.96 (1H, m), 7.76-7.68 (4H, m), 7.64-7.62 (2H, m).

後処理

  1. customdegassed
  2. temperatureThe reaction was heated until the colour
  3. temperaturepale yellow, then cooled
  4. extractionThe products were extracted into ethyl acetate
  5. washThe organic layer was washed with water:brine (1:1, ×5)
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe residue was triturated with isohexane

出典と根拠

ORDレコード
ord-e1dcaa7d07224a34bfef95711daf4f48
出典データセット
uspto-grants-2008_12
特許番号
US07468393B2

反応ノート

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