1-Chloro-4-(2,2-diethoxyethoxy)benzene → 5-Chloro-1-benzofuran
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10](OCC)OCC)=[CH:4][CH:3]=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:8][CH:9]=[CH:10][C:6]=2[CH:7]=1Participants
3
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 1-chloro-4-(2,2-diethoxyethoxy)benzene (45 g, 184 mmol,) in benzene (200 mL) was added polyphosphoric acid (25 g, 221 mmol) with stirring for 2.5 h at 90° C. in an oil bath. The reaction mixture was cooled to room temperature and decanted from the polyphosphoric acid. The solvent was removed under vacuum. The residue was applied onto a silica gel column with 1% ethyl acetate in petroleum ether to afford 5-chlorobenzofuran as colorless oil (14.0 g, crude).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customdecanted from the polyphosphoric acid
- customThe solvent was removed under vacuum
Sources & evidence
- ORD record
- ord-e6798e6a16f347f3a426450d4c6ff285
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912188B2
Reaction notes
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