p-Fluoronitrobenzene → HCID 68464706, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-(3-((tert-butoxycarbonyl)aminomethyl)-4-hydroxyphenyl)acetate (200 mg, 0.677 mmol) was diluted with ACN (2 mL) followed by the addition of K2CO3 (206 mg, 1.49 mmol) and 1-fluoro-4-nitrobenzene (0.103 mL, 0.948 mmol). The reaction mixture was heated to reflux (at about 82° C.) and stirred for 5 hours. The reaction mixture was then diluted with ethyl acetate and water. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a biotage 40S eluting with hexanes/ethyl acetate (3:1) to yield 242 mg of methyl 2-(3-((tert-butoxycarbonyl)aminomethyl)-4-(4-nitrophenoxy)phenyl)acetate as a clear oil.

Provenance & Evidence