F[B-](F)(F)F.C([O+:8]([CH2:11][CH3:12])[CH2:9][CH3:10])C.[Cl:13][C:14]1[CH:22]=C2[C:17]([CH2:18][NH:19]C2=O)=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:11]([O:8][C:9]1[C:10]2[C:17](=[CH:16][CH:15]=[C:14]([Cl:13])[CH:22]=2)[CH2:18][N:19]=1)[CH3:12]A solution of 151 g of triethyloxonium tetrafluoroborate in 3200 ml of methylene chloride was stirred under argon at room temperature for 3.5 hours after the addition of 106.6 g of 6-chloro-2,3-dihydro-1H-isoindol-1-one. The mixture was then treated within 40 minutes with 1.28 l of saturated sodium hydrogen carbonate solution, the organic phase was separated and washed with 1.28 l of water. After drying over sodium sulphate the organic phase was filtered and evaporated. The residue was taken up in 1.3 l of diethyl ether, whereupon it was stirred at room temperature for about 30 minutes. After removing insoluble material by filtration the filtrate was evaporated. There was obtained 110.5 g of 1-ethoxy-6-chloro-3H-isoindole with a m.p. of 64°-66°.
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