Methanol → 1,4-Dibromo-2-methoxybenzene

Participants

Reaction Conditions

Reaction Steps

Add dropwise potassium tert-butoxide (118.2 ml, 118.2 mmol, 1 M in hexane) to a solution of 1,4-dibromo-2-fluorobenzene (25.0 g, 98.5 mmol) in THF (492 mL) and MeOH (40 mL, 984.7 mmol) at RT. Heat the mixture at 70° C. overnight. Quench the mixture with water (50 mL), dilute with Et2O (400 mL), wash once with saturated NH4Cl (300 mL) and back extract the aqueous with Et2O (200 mL). Dry the combined organic phase over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatograph, eluting with 5-10% ethylacetate/hexane to give 22.0 g (84%) of the title compound. GC m/z (79Br81Br) 266 [M]+.

Provenance & Evidence