HCID 66733858, compound → HCID 66733586, compound

Temperature

0 °C

To an ice-cooled solution of 3-(3,5-difluoro-4-methyl-phenyl)-propionic acid butyl ester (2.200 g; 8.584 mmol) in anhydrous THF (20 ml) was added dropwise a 1N solution of BH3.THF complex in THF (13 ml; 13 mmol). The resulting solution was stirred at 0° C., under nitrogen, for 1 h, and then at rt overnight. The reaction mixture was quenched by dropwise addition of MeOH (5 ml) followed by water (10 ml). The volatiles were removed under vacuum, and the product was extracted with DCM (3×20 ml). The combined organic layers were then washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. The crude was purified by FC (DCM/MeOH=12/1) to give the pure product 3-(3,5-difluoro-4-methyl-phenyl)-propan-1-ol as a pale yellow oil (1.440 g; 90%). LC-MS: tR=0.87 min.; [M+H]+: no ionisation.

1. customat rt
2. customovernight
3. customThe reaction mixture was quenched by dropwise addition of MeOH (5 ml)
4. customThe volatiles were removed under vacuum
5. extractionthe product was extracted with DCM (3×20 ml)
6. washThe combined organic layers were then washed with brine
7. dry with materialdried over anh. MgSO4
8. filtrationfiltered
9. concentrationconcentrated to dryness under reduced pressure
10. customThe crude was purified by FC (DCM/MeOH=12/1)

ORD record

ord-9b12885abb4e49caa224f9245b6868f9

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188082B2