Thiophenol → 2-(Phenylthio)benzaldehyde

HRID 1893133ノート

反応式

HRID 1893133 の反応式
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[C:16]1([S:22][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 7969ThiophenolHCID 11430Potassium Carbonate2 回HCID 67970o-Fluorobenzaldehyde

生成物 1

HCID 123406852-(Phenylthio)benzaldehyde収率 71.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

2-fluoro-benzaldehyde (2.00 g, 16.1 mmol), potassium carbonate (2.45 g, 17.7 mmol) and thiophenol (17.1 mmol) were dissolved in 10.0 mL DMF in a 50 mL round-bottomed flask under dry nitrogen, topped with a reflux condenser. The reaction mixture was heated to 80° C. for 24 hrs. After cooling, the mixture was added to 50 mL of saturated potassium carbonate solution and extracted with 3×50 mL portions of ether. The extracts were dried with magnesium sulfate and evaporated. The crude product was further purified by chromatography on silica gel using 9:1 petroleum ether 60-80 and dichloromethane as eluent to give a yellow oil (2.46 g, 71%). 1H NMR (200 MHz, CDCl3): δ 7.07 (dd, J1=7.8, J2=1.2, 1H), 7.27-7.45 (m, 7H), 7.87 (dd, J1=7.3, J2=2.0, 1H), 10.37 (s, 1H) ppm.

後処理

  1. customtopped with a reflux condenser
  2. temperatureAfter cooling
  3. extractionextracted with 3×50 mL portions of ether
  4. dry with materialThe extracts were dried with magnesium sulfate
  5. customevaporated
  6. customThe crude product was further purified by chromatography on silica gel using 9:1 petroleum ether 60-80 and dichloromethane as eluent

出典と根拠

ORDレコード
ord-b6b53b2b820b49fd899f16bc3caa05a2
出典データセット
uspto-grants-2013_08
特許番号
US08513151B2

反応ノート

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