Hydrochloric Acid → (R)-2,2,3,3,3-pentafluoro-1-(4-fluorophenyl)propan-1-ol

Temperature

-78 °C

To a solution of 2,2,3,3,3-pentafluoro-1-(4-fluorophenyl)propan-1-one (13.0 g, 53 mmol) in a mixture 1:1 of dichloromethane and toluene (160 mL) at room temperature, 1M solution of S-methyl-CBS-oxazaborolidine in toluene (5.3 mL, 5.3 mmol) was added at room temperature. The reaction mixture was cooled at −78° C. and catecholborane (7.62 g, 63 mmol) was added. After stirring for 7 h at −78° C., a 4 M solution of HCl in dioxane (18 mL) was added. After allowing the reaction mixture to warm to room temperature, water (5 mL) was added, stirred for 5 min and 10% solution of sodium metabisulfite (25 mL) was added. The heterogeneous mixture was stirred for 15 min and the solid was separated by filtration. The solution was concentrated on rotovap to reduce the amount of dichloromethane and then the residue was diluted with hexanes (100 mL). The resulting solution was washed with a 10% solution of sodium metabisulfite (100 mL) and brine (100 mL). After drying over magnesium sulfate, the solution was concentrated and the crude was purified on a silica gel column, using dichloromethane as eluent to give (R)-2,2,3,3,3-pentafluoro-1-(4-fluorophenyl)propan-1-ol as an oil (12.01 g).

1. temperatureto warm to room temperature
2. stirringstirred for 5 min
3. stirringThe heterogeneous mixture was stirred for 15 min
4. customthe solid was separated by filtration
5. concentrationThe solution was concentrated on rotovap
6. additionthe residue was diluted with hexanes (100 mL)
7. washThe resulting solution was washed with a 10% solution of sodium metabisulfite (100 mL) and brine (100 mL)
8. dry with materialAfter drying over magnesium sulfate
9. concentrationthe solution was concentrated
10. customthe crude was purified on a silica gel column

ORD record

ord-fdfb40c5f92442ca8e3895e9ce3c7987

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07893093B2