2-cyclopentyloxyphenol

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

Procedure: A solution of 2-(cyclopentyloxy)phenol intermediate (5.6 g, 31 mmol) in CH2Cl2 (40 mL) at −78° C. was treated dropwise with a solution of bromine (4.9 g, 31 mmol) in CH2Cl2 (10 mL) via addition funnel over a 1 h period. After warming up to room temperature gradually over 3 h, the reaction was quenched by addition of a saturated aqueous solution of Na2S2O4. The isolated organic layer was washed with water, brine, dried over Na2SO4, filtered, and concentrated. The crude mixture was then purified by ISCO (0-10% EtOAc in hexanes) to afford intermediate 4-bromo-2-(cyclopentyloxy)phenol (2.6 g, 32%) as colorless oil. 1H NMR (300 MHz, CDCl3) 6.97-6.93 (m, 2H), 6.78 (d, J=9.3, 1H), 5.54 (s, 1H), 4.78 (m, 1H), 1.95-1.63 (m, 8H). the reaction was quenched by addition of a saturated aqueous solution of Na2S2O4 The isolated organic layer was washed with water, brine dried over Na2SO4 filtered concentrated The crude mixture was then purified by ISCO (0-10% EtOAc in hexanes)