Water → HCID 46208106, compound

1,3-dichloro-2-(3,5-difluorophenyl)propan-2-ol (1.0 g, 4.15 mmol) was dissolved in acetonitrile (10 ml) and sodium bicarbonate (1.39 g, 16.59 mmol and ethylamine in water (70%, 0.33 ml, 4.15 mmol) was added and the mixture was refluxed for 10 h. Water (50 ml) and tert-butyl methyl ether (50 ml) was added and the organic phase was collected. The aqueous phase was extracted with tert-butyl methyl ether (50 ml, the pooled organic phase was extracted with aqueous hydrochloric acid (10%, 50 ml). The aqueous phase was basified and extracted with tert-butyl methyl ether (2×50 ml), dried (Na2SO4) and evaporated to give 0.35 g crude product. Purification by flash column chromatography on silica gel (ethyl acetate/MeOH 1:0→1:1) gave the title compound (0.2 g, 23%). The amine was converted to the fumaric acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether: M.p. 140-141° C. MS m/z (relative intensity, 70 eV) 213 (M+, 1), 156 (36), 141 (37), 127 (64), 114(50), 58 (bp).

1. temperaturethe mixture was refluxed for 10 h
2. customthe organic phase was collected
3. extractionThe aqueous phase was extracted with tert-butyl methyl ether (50 ml
4. extractionthe pooled organic phase was extracted with aqueous hydrochloric acid (10%, 50 ml)
5. extractionextracted with tert-butyl methyl ether (2×50 ml)
6. dry with materialdried (Na2SO4)
7. customevaporated
8. customto give 0.35 g crude product
9. customPurification by flash column chromatography on silica gel (ethyl acetate/MeOH 1:0→1:1)

ORD record

ord-a0834bdf3981485b9758d92a3517de46

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586572B2