Phenol → HCID 89582694, compound

Participants

Reaction Steps

A solution of 5-bromo-2,3-dihydro-1H-inden-1-ol (1 g, 4.7 mmol), phenol (835 mg, 8.9 mmol) and triphenylphosphine (1.8 g, 6.9 mmol) in anhydrous tetrahydrofuran (70 mL) was stirred at 0° C. under nitrogen atmosphere. To this mixture was added dropwise diisopropyl azodicarboxylate (1.4 g, 6.9 mmol) over 5 minutes. Until TLC indicated that starting material was consumed, the solvent was evaporated in vacuo and the resulting oil was purified by column chromatography (silica gel, hexane/ethyl acetate=1/1) to give the product 5-bromo-1-phenoxy-2,3-dihydro-1H-indene (1.1 g, 85%) as a white solid. LRMS (M+H+) m/z: calcd 288.01. found 288. 1H NMR (300 MHz, CDCl3): δ 7.46-7.27 (m, 6H), 7.02 (s, 1H), 6.99-6.98 (m, 1H), 5.73-5.70 (m, 1H), 3.14-3.09 (m, 1H), 2.96-2.95 (m, 1H), 2.59-2.54 (m, 1H), 2.27-2.23 (m, 1H).

Provenance & Evidence