Allyl bromide → HCID 58963168, compound

Participants

Reaction Steps

Allyl bromide (0.92 mL, 10.7 mmol) was added drop wise over 5 min to vigorously stirred mixture of 2-(4-cyanophenylamino)-2-(3-bromo-5-ethyl-4-hydroxyphenyl)acetate 3 (3.8 g, 9.76 mmol), Cs2CO3 (3.5 g, 10.74 mmol) and DMF (40 mL). The mixture was stirred vigorously for 4 h, then poured into ½-saturated NH4Cl (400 mL). The mixture was extracted with Et2O (3×100 mL). The combined organic layers were washed with water (3×50 mL), brine (1×100 mL), dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography (SiO2, gradient elution 10–15–20% ethyl acetate/hexanes) to yield 3.4 g (81%) of methyl 2-(4-cyanophenylamino)-2-(4-(allyloxy)-3-bromo-5-ethylphenyl)acetate 4 as a colorless solid.

Provenance & Evidence