Methanol → Methyl 2-(4-bromophenyl)acetate

A solution of 202.78 g 4-bromophenylacetic acid in 1.5 L methanol was treated with 15 mL concentrated sulfuric acid and the resulting mixture refluxed under nitrogen for 3 hours. Almost all of the methanol was removed by distillation. Dilute the residue with 1 L ether. Separate the bottom layer and extract that with 2×100 mL ether. Wash the combined ether solution with 3×250 mL 5% NaHCO3 and 250 mL saturated brine, dried over Na2SO4, and concentrated under reduced pressure to give a crude product as light tan oil. Filter that through 300 g silica gel with 10% EtOAc in hexanes and concentrated under reduced pressure to give the title compound as colorless oil. 1H NMR (CDCl3, 500 MHz) δ 7.46˜7.48 (m, 2H), 7.16˜7.19 (m, 2H), 3.72 (s, 3H), 3.60 (s, 2H).

1. temperaturethe resulting mixture refluxed under nitrogen for 3 hours
2. customAlmost all of the methanol was removed by distillation
3. additionDilute the residue with 1 L ether
4. customSeparate the bottom layer
5. extractionextract that with 2×100 mL ether
6. washWash the combined ether solution with 3×250 mL 5% NaHCO3 and 250 mL saturated brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under reduced pressure
9. customto give a crude product as light tan oil
10. filtrationFilter that through 300 g silica gel with 10% EtOAc in hexanes
11. concentrationconcentrated under reduced pressure

ORD record

ord-cd0dc33ef1cd46feab8ce5dd649e9ad6

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989475B2