Methanol → Methyl (4-chloro-3-fluorophenyl)acetate

A solution of 2-(4-chloro-3-fluorophenyl)acetic acid (10.07 g, 53.4 mmol) and concentrated H2SO4 (0.297 mL, 5.34 mmol) in MeOH (200 mL, 4940 mmol) was stirred at 95° C. for 17 hours in a 350 mL sealed vessel. The solution was concentrated in vacuo and then made basic with 1N NaOH(aq) (100 mL). The resulting mixture was extracted with EtOAc (2×100 mL), washed with water (100 mL), and then washed with brine (75 mL). The combined organic layers were dried over MgSO4, concentrated, and dried in vacuo to give methyl 2-(4-chloro-3-fluorophenyl)acetate (10.80 g). MS m/e=203.2 (M+H)+.

1. customsealed vessel
2. concentrationThe solution was concentrated in vacuo
3. extractionThe resulting mixture was extracted with EtOAc (2×100 mL)
4. washwashed with water (100 mL)
5. washwashed with brine (75 mL)
6. dry with materialThe combined organic layers were dried over MgSO4
7. concentrationconcentrated
8. customdried in vacuo

ORD record

ord-f82be1e1a5c44e0fab8b2ac2ca7c74d8

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07635715B2