Methanol → Methyl 2-(3,5-difluoro-4-hydroxyphenyl)acetate

Tribromoborane (2.357 mL, 24.93 mmol) was added dropwise to 2-(3,5-difluoro-4-methoxyphenyl)acetic acid (0.84 g, 4.16 mmol) in dichloromethane (5 mL) at ambient temperature under nitrogen. The resulting solution was stirred at ambient temperature for 16 hours. Methanol (8.41 mL, 207.76 mmol) was added dropwise (—care reaction is vigorous and exothermic—mixture maintained a reflux during the addition) and the mixture was stirred for a further 20 minutes. The reaction mixture was evaporated to dryness and redissolved in DCM (50 mL), and washed sequentially with saturated NaHCO3 (50 mL) and water (50 mL). The organic layer was dried by passing through a phase seperating cartridge and evaporated to afford desired product methyl 2-(3,5-difluoro-4-hydroxyphenyl)acetate (0.660 g, 79%).

1. custom—care reaction
2. temperatureexothermic—mixture maintained
3. temperaturea reflux during the addition) and the mixture
4. stirringwas stirred for a further 20 minutes
5. customThe reaction mixture was evaporated to dryness
6. dissolutionredissolved in DCM (50 mL)
7. washwashed sequentially with saturated NaHCO3 (50 mL) and water (50 mL)
8. customThe organic layer was dried
9. customseperating cartridge
10. customevaporated

ORD record

ord-ab0d54df467d476a8a6475470d63a79d

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188092B2