4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → Methyl 7-(4-hydroxyphenyl)-1-naphthalenecarboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 7-{[(trifluoromethyl)sulfonyl]oxy}-1-naphthalenecarboxylate (1.00 g, 3.0 mmol), tetrakistriphenylphosphine palladium (142 mg, 0.12 mmol) and 4-(4,4,5,5-tetramethyl 1,3,2-dioxaborolan-2-yl-) phenol (799 mg, 3.6 mmol) in a mixture of 1,2-dimethoxyethane (16 mL) and 2M aqueous Na2CO3 (13 mL) was heated in a 70° C. oil bath for 90 minutes. The solution was partitioned between ethyl acetate and water. The organic layer was dried with magnesium sulfate, filtered, and concentrated. The crude material was purified by chromatography on silica gel, hexane to 3:7 ethyl acetate:hexanes, to provide the title compound (0.648 g, 77.7%). 1H NMR (DMSO-d6): δ 9.65 (s, 1H), 8.94 (s, 1H), 8.18-8.13 (m, 2H), 8.05 (d, J=8 Hz, 1H), 7.85 (dd, J=2, 9 Hz; 1H), 7.60 (d, J=9 Hz, 2H), 7.56-7.53 (m, 1H), 6.90 (d, J=9 Hz, 2H), 3.93 (s, 3H).

Provenance & Evidence