Water → 1-Amino-2-bromo-6-tert-butoxy-4-nitronaphthalene

Participants

Reaction Steps

To a stirred solution of 1-amino-6-tert-butoxy-4-nitronaphthalene, as described above in Step E, (2.02 g, 7.76 mmol) in acetic acid (55 mL) was added N-bromosuccinimide (1.45 g, 8.15 mmol), portionwise. The reaction mixture was stirred at ambient temperature for 1 hour, then H2O (150 mL) and CH2Cl2 (300 mL) were added and the organic layer was extracted. The organic extract was washed with saturated aqueous Na2CO3 (2×100 mL), then brine (100 mL), then dried over Na2SO4, filtered, and concentrated in vacuo. The residue was triturated with hexane-Et2O to provide the titled product.

Provenance & Evidence