Oxalyl chloride → HCID 21950065, compound

Participants

Reaction Steps

Step E (1): To a solution of 6-bromo-1H-indole (1.4 g, 7.14 mmol) in Et2O (15.0 mL) was added oxalyl chloride (1.18 g, 9.29 mmol) dropwise at 0° C. under N2. The reaction mixture was stirred at rt for 4 h. An orange precipitate formed, then 40 mL of saturated NaHCO3 was added. The mixture was then stirred at 80° C. for 30 min. Et2O was added to extract the unreacted starting materials. The resulting aqueous layer was acidified with concentrated HCl, and the product precipitated. The solid was filtered and dried to give 1.6 g (yield 83.6%) of 2-(6-bromo-1H-indol-3-yl)-2-oxoacetic acid. MS (ESI) (M−H)+=265.98. 1H-NMR(500 MHz, CD3OD) δ 8.39-8.78 (m, 1 H), 8.21 (d, J=8.24 Hz, 1 H), 7.69 (s, 1 H), 7.40 (d, J=8.55 Hz, 1 H).

Provenance & Evidence