Thiophene → 4-(Thiophen-2-yl)benzaldehyde

HRID 380229

反応式

HRID 380229 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[S:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.C([O-])(=O)C.[K+]>CC(N(C)C)=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 8030ThiopheneHCID 707414-BromobenzaldehydeHCID 517044Potassium Acetate

生成物 1

HCID 7364994-(Thiophen-2-yl)benzaldehyde

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

3.7 g (20 mmol) of 4-bromobenzaldehyde, 9.5 ml (120 mmol) of thiophene, 2.94 g (30 mmol) of potassium acetate and 1.16 g (1 mmol) of tetrakis(triphenylphosphine)-palladium (Fluka, Buchs, Switzerland) in 50 ml of dimethylacetamide are placed in a pressure reactor and stirred at 150° C. under nitrogen for 16 hours. The reaction mixture is concentrated by evaporation; the residue is taken up in water and extracted three times with methylene chloride. After removal of the solvent, the residue is chromatographed on silica gel (hexanelethyl acetate 4:1). The title compound is obtained in the form of a yellow solid. TLC: Rf=0.36 (hexane/ethyl acetate 4:1). HPLC20-100: tRet=15.26. 1H-NMR (CD3OD; 200 MHz): 9.98/s (1H); 7.93 and 7.85/each d, J=9.5 (2×2H); 7.60/d, J=2.5 (1H); (1H); 7.17/d×d, J=2.5 and 5 (1H).

後処理

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. extractionextracted three times with methylene chloride
  3. customAfter removal of the solvent
  4. customthe residue is chromatographed on silica gel (hexanelethyl acetate 4:1)

出典と根拠

ORDレコード
ord-d5e9ce415f7e4d718723cd7f11006b16
出典データセット
uspto-grants-2001_10
特許番号
US06300519B1

関連ノート

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