Ethyl Acetate → HCID 57949818, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-bromomethyl-6-chloro-benzoic acid methyl ester (1.06 g, 3.00 mmol), 4-methoxy-benzylamine (0.521 mL, 4.0 mmol), and K2CO3 (0.967 g, 7.0 mmol) in toluene (7 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-bromo-7-chloro-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.365 g, 33%). GC-MS: m/z 367 (M)+, 336 (M−31)+. 1H NMR (300 MHz, CDCl3): δ (ppm) 3.79 (S, 3H), 4.20 (s, 2H), 4.70 (s, 2H), 6.85 (d, 2H) 7.27 (d, 2H), 7.42 (s, 1H), 7.57 (s, 1H).

Provenance & Evidence