Sodium Carbonate → 3-(Pyridin-3-yl)phenol

Participants

Reaction Steps

A mixture of diethyl(3-pyridyl)borane (11.80 g, 80.0 mmol), 3-bromophenol (16.60 g, 96.0 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), and Na2CO3 (17.0 g, 160.0 mmol) in toluene/water/ethanol (160/80/40 mL) was purged with nitrogen for 5 min and then heated at reflux under nitrogen for 2 h. After solvent removal, the aqueous residue was partitioned between ethyl acetate/brine (400/250 mL). The separated organic layer was washed with brine, filtered, and concentrated. The solid residue was taken up in 130 mL of 3 M HCl, stirred for 15 min, diluted with brine (150 mL), and extracted with ethyl acetate (2×250 mL). The separated aqueous layer was cooled in ice/water bath, adjusted to pH 10 with solid NaOH and Na2CO3, and extracted with ethyl acetate (2×300 mL). The organic extract was dried over sodium sulfate and concentrated to give 12.60 g (92%) of 3-pyridin-3-yl-phenol as a light yellow solid: 1H NMR (CDCl3) δ 6.99 (m, 1H), 7.08 (m, 1H), 7.22 (m, 1H), 7.36 (m, 1H), 7.43 (m, 1H), 8.00 (dd, 1H), 8.60 (d, 1H), 9.00 (s, 1H); MS m/z (relative intensity) 171 (M+, 100), 142 (17), 115 (21).

Provenance & Evidence