2-Bromopyridine → 2-Phenylacetophenone

Participants

Reaction Conditions

Reaction Steps

A solution of 1.2 equivalents of the appropriate picoline or bromopyridine in ether at -78° C. under nitrogen was treated with 1 equivalent of N-butyllithium in hexane and then stirred one hour without cooling to generate the anion. The reaction was again cooled to -78° C. and an ether solution containing 1 equivalent of the appropriate N-methoxy-N-methylamide from procedure 1 was added dropwise. After the addition was complete the reaction was allowed to come to room temperature and stirred for 3 hr. Any excess butyllithium was quenched with isopropyl alcohol at -78° C., water was added at room temperature, and the ether was stripped off. The product was treated with excess 0.25M NaOH, extracted into methylene chloride, and stripped.

Provenance & Evidence