Diethylaniline-borane → HCID 86705523, compound

Temperature

40 °C

A solution of (R)-1-methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole (0.83 mL, 1.4 mmol) and borane diethylaniline (2.5 mL, 14 mmol) in MTBE (25 mL) prepared at RT and heated to 40° C. A solution of 2-bromo-1-(3-fluoro-4-(trifluoromethyl)phenyl)ethanone (143a, 4.0 g, 14 mmol, CASRN 54429-22-3) and MTBE (30 mL) was added dropwise to the above solution and the reaction was stirred at 40° C. for 30 min. The reaction was quenched by adding MeOH followed by 1M HCl and the reaction mixture was then poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with EtOAc/hexane (9:1) to afford 3.2 g (79%) of (R)-2-bromo-1-(3-fluoro-4-(trifluoromethyl)phenyl)ethanol (258).

1. customThe reaction was quenched
2. additionby adding MeOH
3. additionthe reaction mixture was then poured into water
4. extractionextracted with DCM
5. dry with materialThe combined organic extracts were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude product was purified by SiO2 chromatography
9. washeluting with EtOAc/hexane (9:1)

ORD record

ord-76296c6edce74e2b814d3aad92a180fa

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133187B2