Allyl bromide → HCID 21163498, compound

Participants

Reaction Conditions

Reaction Steps

A 250 mL round-bottom flask, equipped with a magnetic stir bar, was charged with methyl 4-aminobenzoate (1) (6.04 g, 40 mmol), K2CO3 (11.06 g, 80 mmol) and 85 mL anhydrous DMF. The mixture was cooled to 0° C. and allyl bromide (3.13 mL, 36 mmol) was added dropwise with stirring. After the reaction mixture was heated at 60° C. for 12 hours, DMF was removed under high vacuum. The residual was extracted with CH2Cl2/H2O=150 mL/200 mL, the organic phase was removed and the aqueous phase was then extracted again with CH2Cl2 (150 mL). The combine organic phases were dried over MgSO4. After removal of solvent, the crude product was purified by silica gel chromatography (eluent: Hexane/Ethyl acetate from 100/0 to 100/7) to give compound 2 as a white solid (5.38 g, 78.2% yield). 1H NMR (400 MHz, CDCl3): δ 3.72 (d, 2H), 3.76 (s, 3H), 5.16 (dd, 1H), 5.21 (dd 1H), 5.80-5.85 (m, 1H), 6.50 (d, 2H), 7.80 (d, 2H); 13C NMR (400 MHz, CDCl3): δ 45.89, 51.53, 111.72, 116.80, 118.66, 131.51, 134.29, 144.91, 151.67. MP: 71-73° C.

Provenance & Evidence