Sodium Hydroxide → 2-(3-Fluorophenyl)cyclopropanecarboxylic acid

Participants

Reaction Steps

To a solution of 7 (390 mg, 2.0 mmol) in MeOH (5 mL) was added 2N NaOH (5 mL) slowly. The reaction solution was stirred at room temperature for 2 h then diluted with H2O (25 mL). After extraction with ether (20 mL), the aqueous layer was acidified with 2N HCl (2.1 mL). The resulting solution was extracted with ether (3×40 mL). The combined organic layers were dried over MgSO4 and concentrated to give 8 (325 mg, 1.8 mmol, 99%) as a light yellow oil: 1H NMR (500 MHz, CDCl3) δ 0.87-0.91 (dd, J=6.0, 13.5 Hz, 1H), 1.21-1.29 (m, 1H), 1.39-1.43 (ddd, J=5.0, 6.5, 8.0 Hz, 1H), 1.67-1.72 (m, 1H), 1.90-1.94 (m, 1H), 2.58-2.63 (m, 1H), 6.79-6.82 (dd, J=2.0, 5.5 Hz, 1H), 6.90-6.95 (m, 2H), 7.24-7.28 (m, 1H), 8.90-11.00 (br s, 1H); 13C NMR (125 MHz, CDCl3) δ 17.8, 24.4, 26.9, 31.8, 113.3, 113.5, 113.8, 114.0, 122.30, 122.32, 130.2, 130.3, 142.4, 142.5, 162.2, 164.2, 179.8; LCQ-MS (M−H+) calcd for C10H8FO2 179. found 179.

Provenance & Evidence