Azobisisobutyronitrile → Methyl 4-(bromomethyl)-2-methoxybenzoate

Temperature

70 °C

9.07 g (51.0 mmol) of N-bromosuccinimide and 120 mg of azobis(isobutyronitrile) were added to a solution of 7.64 g (42.4 mmol) of methyl 4-methyl-2-methoxybenzoate in 140 ml of carbon tetrachloride under a stream of nitrogen, and the resulting mixture was stirred at 70° C. for 1 hour. A further 200 mg of azobis(isobutyronitrile) were then added, making a total addition of 320 mg (1.95 mmol). The reaction mixture was then stirred for 1 hour, after which an aqueous solution of sodium sulfite was added to the mixture to decompose any excess of the reagent. The organic phase was concentrated by evaporation under reduced pressure to one-fourth of its original volume. The concentrate was diluted with ethyl acetate, and the diluted solution was washed with a saturated aqueous solution of sodium hydrogencarbonate, with water and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, giving 11.26 of crude methyl 4-bromomethyl-2-methoxybenzoate as a residue.

1. additiona total addition of 320 mg (1.95 mmol)
2. stirringThe reaction mixture was then stirred for 1 hour
3. concentrationThe organic phase was concentrated by evaporation under reduced pressure to one-fourth of its original volume
4. additionThe concentrate was diluted with ethyl acetate
5. washthe diluted solution was washed with a saturated aqueous solution of sodium hydrogencarbonate, with water and with a saturated aqueous solution of sodium chloride, in that order
6. dry with materialafter which it was dried over anhydrous magnesium sulfate
7. customThe solvent was removed by distillation under reduced pressure

ORD record

ord-2d84f47db4554c7bbf0154c68b9193f9

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06040339