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

HRID 380229

Reaction equation

HRID 380229 reaction equation
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

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 707414-BromobenzaldehydeHCID 517044Potassium Acetate

Product 1

HCID 7364994-(Thiophen-2-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-d5e9ce415f7e4d718723cd7f11006b16
Source dataset
uspto-grants-2001_10
Patent number
US06300519B1

Linked notes

Loading…