Ethyl trifluoroacetate → HCID 117942671, compound

Temperature

10 °C

1-Bromo-4-chloro-2-(2-methoxy-ethoxy)-benzene (CAS#1245563-20-5) (5.00 g, 18.8 mmol) was dissolved in THF (30 mL) and cooled to 0° C. i-Propylmagnesium bromide (11.3 mL, 2.0 M in THF, 22.6 mmol) was added dropwise, and the reaction was stirred at 10° C. for 30 min, then warmed to RT for 16 h. The reaction was then cooled to −15° C. and trifluoroacetic acid ethyl ester (3.37 mL, 28.2 mmol) was added. The reaction was stirred at 10° C. for 1 h. The reaction was quenched with HCl (2 N, 38 mL) at 0° C. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, then concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtOAc/heptane) provided 1-(4-chloro-2-(2-methoxyethoxy)phenyl)-2,2,2-trifluoroethanone.

1. additionwas added dropwise
2. temperaturewarmed to RT for 16 h
3. temperatureThe reaction was then cooled to −15° C.
4. stirringThe reaction was stirred at 10° C. for 1 h
5. customThe reaction was quenched with HCl (2 N, 38 mL) at 0° C
6. additionThe reaction mixture was diluted with water
7. extractionextracted with EtOAc
8. washThe combined organic layers were washed with brine
9. dry with materialdried over Na2SO4
10. concentrationconcentrated in vacuo
11. customPurification by normal phase silica gel column chromatography (EtOAc/heptane)

ORD record

ord-552ca2c7f7b5462cbd5b71726b6a786f

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199994B2