Sodium Hydroxide → 4,5-Dibromobenzene-1,2-diamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4,5-dibromo-2-nitroaniline (3.35 g, 11.32 mmol) in EtOAc (150 mL) was added stannous chloride dihydrate (12.8 g, 56.74 mmol), the mixture was stirred at 75° C. for 16 h, then allowed to cool to room temperature and poured into ice-water (about 150 mL). To the mixture was added 1N aq NaOH with vigorous stirring to take the pH to 9 (pH paper). The resulting thick yellow white emulsion was extracted with EtOAc (3×100 mL). The organic extracts were combined, washed with brine (2×50 mL), dried (over Na2SO4) and evaporated to dryness. The residual solid was dried under 1 mmHg at 40° C. for 14 h giving 2.92 g (97%) of 4,5-dibromo-1,2-phenylenediamine as a yellowish powder. Mp 149°-50° C. IR (KBr) 3400, 1623, 1489, 1394, 1271, 868 cm-1. 1H NMR (DMSO-d6) 6.754 (s, 2H), 4.867 (s, 4H).

Provenance & Evidence