Allyl bromide → HCID 21163498, compound

Temperature

0 °C

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.

1. customA 250 mL round-bottom flask, equipped with a magnetic stir bar
2. temperatureAfter the reaction mixture was heated at 60° C. for 12 hours
3. customDMF was removed under high vacuum
4. extractionThe residual was extracted with CH2Cl2/H2O=150 mL/200 mL
5. customthe organic phase was removed
6. extractionthe aqueous phase was then extracted again with CH2Cl2 (150 mL)
7. dry with materialThe combine organic phases were dried over MgSO4
8. customAfter removal of solvent
9. customthe crude product was purified by silica gel chromatography (eluent: Hexane/Ethyl acetate from 100/0 to 100/7)

ORD record

ord-01072d978f5e4fb78c429bab5be601f3

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710099B2