Hydrochloric Acid → HCID 13191806, compound

Participants

Reaction Steps

To a stirred solution of 2,6-dibromopyridine (100 g) in dry ether (1 l) under nitrogen at -70° was added dropwise during 2 hr a solution of n-butyllithium (270 mL, 1.7M in hexane). After an additional 0.5 hr, a solution of p-chlorobenzaldehyde (65 g) in dry ether (500 mL) was added during a 1 hr period. The reaction mixture was allowed to warm to ca. 0° and then poured into aqueous hydrochloric acid (1 l, 4N). The ether layer was separated and the aqueous layer was extracted with two additional portions (300 mL) of ether. The combined ether layers were washed with water (500 mL), dried (Na2SO4) and concentrated to give a syrup. The crude product was chromatographed on silica gel using the Waters Prep 500 (trademark of Waters Associates Inc., Milford, MA 01757) with methylene chloride to provide α-(6-bromo-2-pyridyl)-4-chlorobenzyl alcohol (93.8 g), m.p. 64.5°-65°.

Provenance & Evidence