alpha-Bromo-o-chlorotoluene → 3-(2-Chlorobenzyloxy)-5-methylphenol

Participants

Reaction Steps

To 1.31 g (9.22 mmol) of orcinol monohydrate in 20 mL anhydrous N,N-dimethylformamide under a nitrogen atmosphere was added 220 mg (9.17 mmol) of NaH (100%). After 5 min, 1.30 mL (10.0 mmol) of 2-chlorobenzyl bromide was added. The reaction mixture was stirred for 2 H and then quenched with 1 N HCl. The reaction mixture was extracted into ethyl acetate (200 mL). The organic phase was washed with water (4×100 mL), dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (diethyl ether/hexane (50:50 to 1.00:0) gave 656 mg of the title compound as a glass.

Provenance & Evidence