Dichloromethane → 4-Bromo-2-fluoro-6-hydroxybenzonitrile

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Reaction Steps

To a 500-mL RBF was added 4-bromo-2-fluoro-6-[(phenylmethyl)oxy]benzonitrile (5 g, 16.33 mmol) and CH2Cl2 (100 mL). The flask was cooled in an ice-water bath and BBr3 (49.0 mL, 49.0 mmol) (solution in CH2Cl2) was added dropwise via syringe. The red solution was allowed to warm to room temperature over 1 hour. The solution was poured into water (200 mL) and extracted with EtOAc (3×200 mL). The combined organics were concentrated to a yellow residue. The residue was treated with CH2Cl2, and a precipitate formed which was collected to afford the title compound (2.830 g) as a fine yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 7.03 (t, J=1.4 Hz, 1H), 7.29 (dd, J=9.0, 1.6 Hz, 1H), 12.23 (s, 1H).

Provenance & Evidence