Water → 3-Bromonaphthalene-2,7-diol

Participants

Reaction Conditions

Reaction Steps

To a solution of naphthalene-2,7-diol (5.00 g, 31.3 mmol) in AcOH (25 mL) was added Br2 (3.3 mL, 62.6 mmol) in AcOH (25 mL) dropwise over 15 minutes at 10-15° C., then mixture was stirred at 10-15° C. for 1 hour. Sn powder (7.75 g, 64.6 mmol) and H2O (20 mL) was added and the mixture was heated to 80° C. for 1 hour. The mixture was diluted with ice-water (50 mL), the extracted with EtOAc (30 mL×3), organic was washed with brine (50 mL), dried over Na2SO4, filtered and concentrated. Purification by column chromatography on silica gel (PE/EtOAc=15/1) and further prep-HPLC (0.1% TFA as additive) gave the product (2.0 g, yield 27%) as a solid.

Provenance & Evidence