Thionyl Chloride → Methyl 2-(4-(bromomethyl)phenyl)acetate

Temperatur

0 °C

To a mixture of p-bromomethylphenylacetic acid (50.0 g, 218 mmol) in MeOH (125 g) and toluene (250 g), was added thionyl chloride (15.6 g) dropwise at 0° C. and stirred for 3 hr. Separately NaHCO3 (33 g, 393 mmol) was dissolved in water (540 g), mixed with toluene (200 g) and cooled to 0° C. The reaction solution described above was added dropwise to the mixture and stirred for 1 hr. The aqueous layer was removed and the organic layer washed with water. The solution was then concentrated under reduced pressure at a temperature below 40° C. to give the subtitle compound as a crude product (58.9 g) used directly in the following reaction. 1H NMR (DMSO-d6) δ 7.37 (d, 2H), 7.34 (d, 2H), 4.62 (s, 2H), 3.73 (s, 2H), 3.63 (s, 3H)

1. additionabove was added dropwise to the mixture
2. stirringstirred for 1 hr
3. customThe aqueous layer was removed
4. washthe organic layer washed with water
5. concentrationThe solution was then concentrated under reduced pressure at a temperature below 40° C.

ORD-Eintrag

ord-6c511b199ecd4ff0a0654ecc319f86ea

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08895570B2