Trimethyl orthoformate → 2-Bromo-5-(dimethoxymethyl)pyridine

Participants

Reaction Steps

Trimethyl orthoformate (643 μl, 5.9 mmol) and p-toluene sulphonic acid monohydrate (102 mg, 0.54 mmol) were added to 6-bromo-pyridine-3-carbaldehyde (1 g, 5.37 mmol) dissolved in MeOH (40 ml). The mixture was stirred for 24 h at room temperature and then partitioned between water and Et2O. The organic extract was washed with water, 5% Na2CO3, dried over Na2SO4 and evaporated under vacuo to give 1.2 g of 2-bromo-5-dimethoxymethyl-pyridine as a brown oil.

Provenance & Evidence