Bromine → 5-Bromothiophene-2,3-dicarbaldehyde

Participants

Reaction Steps

Bromine (6.0 mL, 116.3 mmol) was added drop wise at room temperature to a solution of 2,3-thiophenedicarboxaldehyde (5.1 g, 36.38 mmol) in 100 mL of CHCl3. The reaction mixture was stirred overnight and then excess bromine was quenched with a saturated solution of Na2S2O3. The organic layer was extracted with CHCl3, dried over Na2SO4 and volatiles were removed in vacuo to obtain 1 as a brown solid. Spectroscopically pure compound was isolated by column chromatography using silica gel as stationary phase and a 4:1 mixture of CH2Cl2:hexanes. 1H NMR (500 MHz, CDCl3): δ1 0.37 (s, 1H), 10.26 (s, 1H), 7.59 (s, 1H).

Provenance & Evidence