isoindol-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-(bromomethyl)benzophenone (138 mg, 0.5 mmol), isoindolone (67 mg, 0.5 mmol), cesium carbonate (407 mg, 1.25 mmol), and 18-crown-6 (13 mg, 0.05 mmol) in acetone (10 mL) was stirred heating at reflux for 3 h. Workup and silica gel column chromatography using a gradient of hexanes to 50% ethyl acetate in hexanes afforded 2-(4-benzoylbenzyl)-2,3-dihydroisoindol-1-one (149 mg, 91%). GC/MS gave: m/z (rel.int.) 327 (M+, 97), 250 (5), 222 (42), 196 (20) 165 (31), 146 (31), 133 (53), 119 (94), 105 (71), 91 (100), and 77 (98). 1H NMR (300 MHz, CDCl3): δ 4.33 (s, 2H), 4.89 (s, 2H), 7.42 (d, 2H), 7.45-7.59 (m, 6H), 7.77 (dd, 4H), 7.91 (dd, 1H). heating at reflux for 3 h

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-(bromomethyl)benzophenone (138 mg, 0.5 mmol), isoindolone (67 mg, 0.5 mmol), cesium carbonate (407 mg, 1.25 mmol), and 18-crown-6 (13 mg, 0.05 mmol) in acetone (10 mL) was stirred heating at reflux for 3 h. Workup and silica gel column chromatography using a gradient of hexanes to 50% ethyl acetate in hexanes afforded 2-(4-benzoylbenzyl)-2,3-dihydroisoindol-1-one (149 mg, 91%). GC/MS gave: m/z (rel.int.) 327 (M+, 97), 250 (5), 222 (42), 196 (20) 165 (31), 146 (31), 133 (53), 119 (94), 105 (71), 91 (100), and 77 (98). 1H NMR (300 MHz, CDCl3): δ 4.33 (s, 2H), 4.89 (s, 2H), 7.42 (d, 2H), 7.45-7.59 (m, 6H), 7.77 (dd, 4H), 7.91 (dd, 1H). heating at reflux for 3 h