p-Toluenesulfonic acid → 3-Bromo-4-(dimethoxymethyl)pyridine

Participants

Reaction Steps

PTSA (834 mg, 4.384 mmol) was added to a solution of 3-bromo-pyridine-4-carbaldehyde (600 mg, 3.2256 mmol) in methanol (20 mL). The resulting mixture was heated to reflux for 4 hours. The reaction was monitored by TLC (20% ethylacetate in hexane). The reaction mixture was concentrated and basified with NaHCO3 solution. The reaction mixture was partitioned between water and DCM. The organic layer was washed with brine solution, dried over Na7SO4, filtered and the filtrate was concentrated to afford 700 mg of 3-Bromo-4-dimethoxymethyl-pyridine (93.5% yield).

Provenance & Evidence