Triacetoxyperiodinane → 5-Bromo-4-methoxy-3-methyl-benzofuran-2-carbaldehyde

Participants

Reaction Steps

To a solution of 0.21 g (0.77 mmole) of 5-bromo-4-methoxy-3-methyl-1-benzofuran-2-yl) methanol (Example 136, Step 1) in 6 mL of dichloromethane, 0.36 g (0.85 mmole, 1.1 eq) of Dess Martin periodinane was added. The reaction was stirred at room temperature for 2 hours and then diluted with 15 mL of ether. To the reaction was added 5 mL of 1NaOH and the mixture was stirred for 30 minutes. The reaction was diluted with ether and water. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated to provide 0.19 g of 5-bromo-4-methoxy-3-methyl-1-benzofuran-2-carbaldehyde. Yield 90.4%; m.p. 81-82° C.; MS: 268.9 (M+H)+.

Provenance & Evidence