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

HRID 1458480

반응식

HRID 1458480 반응식
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

참가 물질

6

반응물 3

HCID 8030ThiopheneHCID 707414-BromobenzaldehydeHCID 517044Potassium Acetate

생성물 1

HCID 7364994-(Thiophen-2-yl)benzaldehyde

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 31374Dimethylacetamide용매

반응 조건

온도
150 °C

실험 절차

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 (hexane/ethyl acetate 4:1). The title compound is obtained in the form of a yellow solid. TLC: Rt 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); 7.52/d, J=5 (1H); 7.17/d×d, J=2.5 and 5 (1H).

후처리

  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 (hexane/ethyl acetate 4:1)

출처 및 근거

ORD 기록
ord-02410a55293242be982f4ecebcfbf643
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849911

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