Pyridine → HCID 21483889, compound

Participants

Reaction Conditions

Reaction Steps

In a four-necked flask fitted with a stirrer, internal thermometer, dropping funnel and calcium chloride tube is placed freshly distilled phosphorous tribromide (9.6 g., 0.036 mole) and dry toluene (50 ml.). To this is added dry pyridine (1.5 g.). The mixture is stirred for 15 minutes and then cooled to -5° C. A mixture of 2-(3,4-dichloro-5-methoxyphenyl)ethanol (22.1 g., 0.1 mole) and dry pyridine (0.5 g.) in toluene (50 ml.) is added dropwise with stirring at -5° to -3° C. over a one hour period. The reaction mixture is stirred at -5° to -3° C. for an additional hour and then allowed to warm up to 20°-25° C. The mixture is kept for 48 hours and then added to ice water (ca. 500 ml.). The toluene layer is separated and washed with water, dilute hydrochloric acid, sodium bicarbonate solution and again with water. After drying over Na2SO4 and evaporation of the toluene under reduced pressure there is obtained 2,3-dichloro-5-(2-bromoethyl)anisole.

Provenance & Evidence