[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([NH:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:11]=2[C:12](OC)=[O:13])[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[Na+].O>C1COCC1>[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([N:8]2[CH2:9][C:10]3[C:11](=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[C:12]2=[O:13])[CH:5]=[CH:6][CH:7]=1Step 3 A solution of methyl 2-((3-bromo-2-methylphenylamino)methyl)-5-methoxybenzoate (360 mg, 0.988 mmol) in THF (10 mL) was treated with sodium tert-butoxide (142 mg, 1.483 mmol) and stirred at rt overnight. The mixture was treated with water and extracted twice with DCM. The combined organic phases were washed with water, dried and concentrated. The residue was purified by column chromatography (eluting with EtOAc-hexane) to provide 2-(3-bromo-2-methylphenyl)-6-methoxyisoindolin-1-one as a white solid (246 mg, 75%). 1H NMR (400 MHz, chloroform-d) δ 7.62 (1 H, dd, J=7.9, 1.1 Hz), 7.46 (1 H, d, J=2.4 Hz), 7.42 (1 H, d, J=8.4 Hz), 7.15-7.26 (3 H, m), 4.67 (2 H, s), 3.92 (3 H, s), 2.34 (3 H, s). Mass spectrum m/z 332, 334 (M+H)+.
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