Triethylamine → HCID 68891239, compound

Participants

Reaction Steps

Oxalyl chloride (5 mL) was added to a solution of 4-bromo-2-methylbenzoic acid (1.1 g, 4.72 mmol) in methylene chloride (20 mL) and DMF (2 drops) and stirred at rt for 1 h. The reaction mixture was concentrated and dried. 2-Bromoethylamine hydrobromide (0.88 g, 4.29 mmol) was dissolved in benzene (20 mL) and triethylamine (3.01 mL; 21.45 mmol) was added. The acid chloride was slowly added to the reaction mixture which was stirred vigorously at 90° C. for 18 h. The reaction mixture was poured into 50 mL of water and the product was extracted with methylene chloride (2×200 mL). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography eluting with 10% ethyl acetate/hexanes, then 15% ethyl acetate/hexanes yielded 0.33 g of the desired product: 1H NMR (500 MHz, CDCl3) δ 7.71 (d, J=8.3 Hz, 1H), 7.43 (s, 1H), 7.39 (d, J=8.4 Hz, 1H), 4.41 (t, J=9.5 Hz, 2H), 4.11 (t, J=9.6 Hz, 2H), 2.60 (s, 3H).

Provenance & Evidence