Thionyl Chloride → 3-Chloro-2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([OH:17])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=O)=[C:4]([F:19])[CH:3]=1.S(Cl)([Cl:22])=O>ClCCl>[Cl:22][CH:9]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=2[C:16](=[O:17])[N:8]1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[F:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In 30 ml of dichloromethane was suspended 21.0 g of 2-(4-chloro-2-fluorophenyl)-3-hydroxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one, and 7.5 ml of thionyl chloride was added to the suspension with stirring over a 20-minute period. The reaction solution was warmed, stirred at 40° to 45° C. for 1 hour and concentrated to dryness under reduced pressure. The residue was dissolved in methylene chloride, and the insoluble matter resulting from the addition of hexane was filtered out. The filtrate was concentrated to dryness under reduced pressure, thereby producing 19.5 g (yield of 87%) of the subject compound as crystals. Recrystallization from cyclohexane yielded white crystals, m.p. 89°-90° C.