Bromine → Ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)acetate

Temperature

-10 °C

To a stirred solution of ethyl 2-(3-chloro-4-hydroxyphenyl)acetate (15 g, 69 mmol) in CCl4 (270 mL), bromine (11.1 g, 69 mmol) was added slowly (dissolved in 140 mL of CCl4) at −10° C. over a period of 30 min. The reaction mixture was stirred for another 1 h at −10° C. Upon completion of the reaction, the mixture was poured onto crushed ice and extracted with DCM (×2). The combined organic layers were washed with saturated Na2S2O3 solution, water, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude compound was purified by re-crystallization using hexane to yield compound ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)acetate (7 g, 7 g starting material recovered) as a white solid.

1. customUpon completion of the reaction
2. additionthe mixture was poured
3. customonto crushed ice
4. extractionextracted with DCM (×2)
5. washThe combined organic layers were washed with saturated Na2S2O3 solution, water
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude compound was purified by re-crystallization

ORD record

ord-b0d8405e25f94ab8ad7cadfbb8697bc3

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08664249B2