p-Toluenesulfonic acid → Methyl 4-bromo-alpha-hydroxybenzeneacetate

Temperatur

55 °C

To a solution of 2-(4-bromophenyl)-2-hydroxyacetic acid (5.0 g, 22 mmol) in MeOH (10 mL) was added 2,2-dimethoxypropane (3.4 g, 33 mmol) and 4-methylbenzene-1-sulfonic acid (2.0 mg, 0.010 mmol). The resulting solution was stirred overnight at 55° C. and allowed to cool to rt. The resulting mixture was concentrated under reduced pressure and poured into water (100 mL). The solids were collected by filtration and washed with hexanes (2×20 mL) to obtain compound 50a as a gray solid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.54-7.51 (m, 2H), 7.35-7.28 (m, 2H), 5.18-5.16 (m, 1H), 3.793 (s, 3H), 3.51-3.49 (m, 1H).

1. temperatureto cool to rt
2. concentrationThe resulting mixture was concentrated under reduced pressure
3. additionpoured into water (100 mL)
4. filtrationThe solids were collected by filtration
5. washwashed with hexanes (2×20 mL)

ORD-Eintrag

ord-f3e6ec73f897426aa199a0c9f89ac2fe

Quelldatensatz

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09193736B2