Sodium hydride → 5-Bromo-1-chloro-3-ethyl-2-(2-methoxy-ethoxymethoxy)-benzene

Participants

Reaction Steps

A solution of 4-Bromo-2-chloro-6-ethyl-phenol dissolved in THF (10 mL) was added to a cooled 0° C. suspension of NaH (0.43 g, 10.8 mmol, 60% dispersion in mineral oil) in THF (20 ml). After the addition was complete the reaction mixture was warmed up to room temperature and stirred for 30 mins. 2-Methoxyethoxymethyl chloride (1.34 mL, 11.7 mmol) was added and the reaction was stirred for 15 hours. The reaction mixture was quenched with 1N HCl and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a yellow oil. Purification by flash column chromatography (0% to 10% EtOAc in hexanes) gave the title compound as a clear oil (2.4 g, 76%). 1H NMR (400 MHz, CDCl3): δ 1.21 (t, J=7.3 Hz, 3 H), 2.70 (q, J=7.6 Hz, 2 H), 3.40 (s, 3 H), 3.61 (m, 2 H), 3.98 (m, 2 H), 5.15 (s, 2 H), 7.24 (s, 1 H), 7.37 (s, 1 H).

Provenance & Evidence