Toluene → Ethyl 2-(5-fluorobenzofuran-3-yl)acetate
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7](=O)[C:6]=2[CH:11]=1.[C:12]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:14])=[O:13].[C:35]1(C)C=CC=C[CH:36]=1>>[CH2:35]([O:14][C:12](=[O:13])[CH2:15][C:7]1[C:6]2[CH:11]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:9][CH:8]=1)[CH3:36]Participants
4
Procedure
A mixture of 5-fluoro-benzofuran-3 (2H)-one (1.52 g, 10 mmol) and (carboxymethylene)triphenylphosphorane (5.22 g, 15 mmol) was refluxed in toluene (100 ml) for 48 hrs. At the end, reaction mixture was concentrated and loaded over a silica-gel column. The column was eluted with hexane (500 ml) and later with 25% ethyl acetate. The product, ethyl(5-fluoro-1-benzofuran-3-yl)acetate, was obtained as a white oil. Yield: 1.8 g (80%); 223 (M+H).