1-Octanethiol → Benzenepropanoic acid, alpha,alpha-difluoro-4-hydroxy-, ethyl ester

To a solution of ethyl 2,2-difluoro-3-(4-methoxyphenyl)propanoate (1.72 g, 7.05 mmol) synthesized according to the method described in Synthesis, vol. 13, pp. 1917-1924 (2000) and aluminum chloride (2.82 g, 21.2 mmol) in dichloromethane (50 mL) was added dropwise 1-octanethiol (2.06 g, 14.1 mmol) and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into ice water and the mixture was stirred for 30 min. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (8%-60% ethyl acetate/hexane) to give the title compound (0.90 g, yield 56%) as a colorless oil.

1. customdescribed in Synthesis, vol. 13
2. stirringthe mixture was stirred for 30 min
3. customThe organic layer was separated
4. washwashed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (8%-60% ethyl acetate/hexane)

ORD record

ord-f35fa98b1d6d439b869c13c2caf8658e

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456218B2