Carbon Dioxide → 5-Bromothiophene-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

THF (50 mL) was added via cannula to a flame-dried 100 mL Schlenk flask. 2,5-dibromothiophene (10 mmol, 2.42 g) was added via syringe. Reaction vessel was cooled to −78° C. and n-butyllithium (1.61M solution in hexanes, 11 mmol, 6.8 mL) was added dropwise over 5 minutes. The solution was allowed to stir at −78° C. for 1 hr. Dry ice (approx. 50 g) was added to the reaction mixture, and was allowed to stir and return to room temperature for 18 hrs. under nitrogen. The light gray suspension was filtered and the white solid was stirred in 2M HCl for 1 hr. The suspension was filtered to yield a white solid (5.7 mmol, 1.2 g, 57%). 1H NMR (400 MHz, CDCl3) δ: 11.45 (br s, 1H), 7.64 (d, 1H, J=4.0 Hz), 7.11 (dd, 1H, J=4.0 Hz).

Provenance & Evidence