1,1-Dichloroethane → HCID 14234687, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-amino-m-cresol (1.0 g, 8.1 mmol) in 10 mL of dry dichloroethane is add to a prestirred solution of 2-bromo-3-methylbutyic acid (1.61 g, 8.9 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.71 g, 8.9 mmol) in 20 mL of dry dichloroethane. The reaction stirred overnight before quenching with water (50 mL) and extracting with chlrorform (3×50 mL). The combined organic layers were dried with sodium sulfate, filtered and excess solvent removed on the rotary evaporator. The crude solid was then dissolved in 15 mL of dry DMF and treated with cesium carbonate (5.86 g, 18 mmol) and heated to 80° C. for 6 hours. The reaction mixture was then cooled and quenched with 50 mL of water and extracted with chloroform (3×50 mL). The combined organic layers were dried with sodium sulfate, filtered and excess solvent removed on the rotary evaporator. The crude product was then purified using flash chromatography (10% EtOAc/hexanes) to yield 1.08 g (65%) of product as an off white solid. MS (electrospray): mass calculated for C12H15NO2, 205.11; m/z found 206.1 [M+H]+.

Provenance & Evidence