Water → HCID 15867527, compound

Participants

Reaction Conditions

Reaction Steps

Add boron tribromide (305.6 mL, 305.6 mmol) dropwise while maintaining the temperature below 0° C. to a solution of tert-butyl 3-methoxy-2-propyl-benzoate (61.2 g, 244 mmol) in toluene (428 mL) which has been cooled to −25° C. Stir at −5° C. for 3 h. Add water (100 mL) dropwise, raising the temperature to 7° C., and stir 30 min. Concentrate the mixture in vacuo and then suspend the semisolid in water (200 mL). Stir 1 h and filter the suspension through a glass frit. Wash the collected solid with water and dry the solid to yield the title compound (43.1 g, 98%). 1H NMR (300 MHz, CDCl3) δ 7.58 (d, J=8.0 Hz, 1H); 7.16 (t, J=8.0 Hz, 1H); 6.99 (d, J=7.7 Hz, 1H); 5.0 (bs, 2H); 2.98 (t, J=7.7 Hz, 2H), 1.64 (m, 2H); 1.02 (t, J=7.4 Hz, 3H).

Provenance & Evidence