4-Methylphenyl acetate → 4-(Bromomethyl)phenyl acetate

Temperature

80 °C

Into a reaction flask equipped with a mechanical stirrer, thermometer and reflux apparatus was charged 75 grams (0.5 moles) of p-methylphenyl acetate prepared in Part A, 88 grams (0.5 moles) of N-bromosuccinimide, 300 milliliters of carbon tetrachloride and 1.0 gram of benzoyl peroxide. The resulting reaction mixture was carefully heated to 80° C. with a mantle, at which temperature, slight reflux ensued along with an exothermic reaction. Reflux was carefully maintained for 40 minutes and then 200 milliliters of carbon tetrachloride was gradually added to the reaction flask and the reaction mixture was then cooled to 25° C. (total time from onset of reflux was 50 minutes). The reaction mixture was filtered on a Buchner funnel and after the collected solid (succinimide) was washed four times with 100 milliliters of carbon tetrachloride, the total carbon tetrachloride solution (filtrate and washes) was stripped on a rotary evaporator. The resulting residue was distilled at reduced pressure (0.4 torr) to give a total of 92.8 grams of the desired product, whose nuclear magnetic resonance (NMR) spectrum was consistent with bromination of the aromatic methyl group: 2.13δ, singlet, CH3O; 4.28, singlet, BrCH2 --; and 6.97, quartet, aromatic protons.

1. customInto a reaction flask equipped with a mechanical stirrer
2. temperaturethermometer and reflux apparatus
3. customThe resulting reaction mixture
4. temperatureslight reflux
5. customensued along with an exothermic reaction
6. temperatureReflux
7. temperaturewas carefully maintained for 40 minutes
8. temperaturethe reaction mixture was then cooled to 25° C.
9. temperature(total time from onset of reflux was 50 minutes)
10. filtrationThe reaction mixture was filtered on a Buchner funnel
11. washafter the collected solid (succinimide) was washed four times with 100 milliliters of carbon tetrachloride
12. customthe total carbon tetrachloride solution (filtrate and washes) was stripped on a rotary evaporator
13. distillationThe resulting residue was distilled at reduced pressure (0.4 torr)

ORD record

ord-e36d4907812d47f7a9b01820aabb356a

Source dataset

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04841009