1,2-Dichlorobenzene → HCID 15029656, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([O:20]CC=C)[C:12]=3[C:13]=2[CH3:14])=[O:8])=[CH:5][CH:4]=1.Cl[C:27]1[CH:32]=CC=C[C:28]=1Cl>>[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([C:7]([C:9]2[O:10][C:11]3[C:18]([CH2:32][CH:27]=[CH2:28])=[CH:17][C:16]([Cl:19])=[C:15]([OH:20])[C:12]=3[C:13]=2[CH3:14])=[O:8])=[CH:5][CH:4]=1Participants
3
Procedure
A mixture of 2-(p-methoxybenzoyl)-3-methyl-4-allyloxy-5-chlorobenzofuran (400 mg; 1.12mmoles) in ortho-dichlorobenzene (15 mL) was refluxed under nitrogen for 1.5 hours. The reaction mixture was cooled to room temperature and purified by chromatography on silica gel using 20% ethylacetate as eluent to yield 110 mg (27%) of 2-(p-methoxybenzoyl)-3-methyl-4-hydroxy-5-chloro-7-allylbenzofuran.
Workup
- temperaturewas refluxed under nitrogen for 1.5 hours
- custompurified by chromatography on silica gel using 20% ethylacetate as eluent