Allyl bromide → Methyl 3-allyloxy-4-nitro-benzoate

Methyl 3-hydroxy-4-nitro-benzoate 1b (7 g, 35.50 mmol) was dissolved in 100 mL of anhydrous acetonitrile followed by the addition of potassium carbonate (14.70 g, 106.50 mmol) and 3-bromopropene (6.2 mL, 71 mmol) successively, the reaction mixture was heated to reflux for 3 hours with stirring. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. The crude residue was added with 150 mL of ethyl acetate, washed with water (100 mL×3) and saturated sodium chloride solution (100 mL×3) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound methyl 3-allyloxy-4-nitro-benzoate 1c (7.45 g, yield: 89.0%) as a yellow solid.

1. temperaturethe reaction mixture was heated
2. temperatureto reflux for 3 hours
3. filtrationThe resulting mixture was filtered
4. concentrationthe filtrate was concentrated under reduced pressure
5. additionThe crude residue was added with 150 mL of ethyl acetate
6. washwashed with water (100 mL×3) and saturated sodium chloride solution (100 mL×3) successively
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-363b3bd7494e49c1b823fdf9c35f537e

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691822B2