methyl 4-fluoro-2-formylbenzoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 3.4 g (0.02 mole) 2-carboxy-5-fluorobenzaldehyde (the product of Example 6) and 5.0 g [3.75 ml (0.04 mole)] dimethyl sulfate in methylene chloride was heated to reflux. The heating mantle was removed; and triethylamine, 4.15 g [5.7 ml (0.04 mole)] was added dropwise at a rate which maintained a brisk reflux. After the addition was complete, the reaction mixture was allowed to cool and was stirred at room temperature over the weekend. The reaction mixture was poured into water; the layers were separated. The methylene chloride layer was washed with a sodium bicarbonate solution, dried and evaporated to give 2.5 g of the above-identified product as a yellow oil. was heated to reflux The heating mantle was removed and triethylamine, 4.15 g [5.7 ml (0.04 mole)] was added dropwise at a rate which maintained a brisk reflux After the addition to cool The reaction mixture was poured into water the layers were separated The methylene chloride layer was washed with a sodium bicarbonate solution dried evaporated