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

HRID 1351657

반응식

HRID 1351657 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-38ca2c63ebc34dd4ad58df02e7fe49f2
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217740B2

연결된 노트

불러오는 중…