3-Iodobenzaldehyde → 3-[(4-Bromophenyl)sulfonyl]benzaldehyde

HRID 2376972

反応式

HRID 2376972 の反応式
I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.[Na+]>CS(C)=O.C(OCC)(=O)C.[Cu]I>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])(=[O:19])=[O:18])=[CH:13][CH:12]=1

参加物

6

反応物 2

HCID 2526103-IodobenzaldehydeHCID 23670685Sodium 4-bromobenzene-1-sulfinate

生成物 1

HCID 210994843-[(4-Bromophenyl)sulfonyl]benzaldehyde収率 35.8%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

3-Iodobenzaldehyde (1.0 g, 4.3 mmol), copper(I) iodide (2.45 g, 12.9 mmol) and sodium 4-bromophenylsulfinate (1.55 g, 5.59 mmol) were combined in dimethylsulfoxide (8.6 mL) and heated to 110° C. for 4 hours. The cooled reaction mixture was diluted with ethyl acetate and filtered through Hyflo®. The filtrate was washed with water (×2) and brine and dried over MgSO4. The solvent was removed in vacuo and the residue purified by flash column chromatography on silica, eluting with 25% ethyl acetate/isohexane, to give 3-[(4-bromophenyl)sulfonyl]benzaldehyde (0.5 g, 35%). δH (400 MHz, d6 DMSO): 10.09 (1H, s), 8.47-8.44 (1H, m), 8.29-8.25 (1H, m), 8.21 (1H, d, J=7.6 Hz), 7.96-7.94 (2H, m), 7.88-7.84 (3H, m).

後処理

  1. customThe cooled reaction mixture
  2. filtrationfiltered through Hyflo®
  3. washThe filtrate was washed with water (×2) and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo
  6. customthe residue purified by flash column chromatography on silica
  7. washeluting with 25% ethyl acetate/isohexane

出典と根拠

ORDレコード
ord-af8db577ad0f43fdbb932ca23d6058de
出典データセット
uspto-grants-2008_12
特許番号
US07468393B2

関連ノート

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