Chlorosuccinimide → HCID 13339542, compound

Participants

Reaction Conditions

Reaction Steps

1-(3-Fluoro-4-methoxyphenyl)indole (7.0 g, 0.029 mole), N-chlorosuccinimide (98%, 4.14 g, 0.0304 mole) and CH2Cl2 (200 ml) were combined and stirred 2 hours at 25° C., producing a solution which was evaporated in vacuo to a semisolid. The latter was diluted with 120 ml CH3CO2H and warmed to 70°. H3PO4 (85%, 31.3 ml) was added in one portion, the mixture was refluxed 1 hour, cooled, basified with saturated Na2CO3 and extracted 4×100 ml ethyl acetate. The organic layers were combined, dried over MgSO4, and evaporated in vacuo to solids (7.9 g). Chromatography on silica gel, (7.5×15 cm) eluting with CH2Cl2 in 1 liter fractions gave, on evaporation of combined fractions 4-13, purified title product, 3.8 g, m.p. 133°-136°.

Provenance & Evidence