3-Bromotoluene → HCID 22101820, compound

Participants

Reaction Steps

n-Butyllithium (2.5 solution in hexanes, 3.9 ml) was added dropwise to a stirred solution of 3-bromotoluene (1.1 ml) in dry tetrahydrofuran (20 ml) at -70° C. under an atmosphere of dry nitrogen. After 20 minutes, 4-methyl-5-oxazolecarbaldehyde (1.15 g) in tetrahydrofuran (10 ml) was added. After 1 hour the mixture was allowed to warm to room temperature and was then heated under reflux for 1 hour. The cooled solution was poured into saturated aqueous sodium hydrogen carbonate. Extraction with ethyl acetate and flash chromatography then gave the title compound. M.p. 76.5°-77.5° C.

Provenance & Evidence