Borane → 3-(4-Fluorophenoxy)propan-1-ol

Temperature

5 °C

3-(4-Fluorophenoxy)propanoic acid (16.6 g, 90 mmol) was stirred in 100 mL of tetrahydrofuran under a nitrogen atmosphere. The solution was cooled to 5° C. and borane (120 mL, 120 mmol, 1M in tetrahydrofuran) was added dropwise at a rate to keep the temperature of the reaction near 5° C. Once the addition was complete, the solution was allowed to stir at room temperature overnight. The reaction was then cooled below 10° C. and 18 mL of a tetrahydrofuran/water mixture was added. The tetrahydrofuran was removed by evaporation under reduced pressure and the resulting cloudy mixture was diluted with about 200 mL of water. This mixture was extracted three times with diethyl ether. The combined extracts were washed with water, twice with 10% aqueous sodium bicarbonate, and once with brine. The combined extracts were then dried over sodium sulfate, filtered, and concentrated to give 15.24 g of a product oil. Yield: 99%. MS(FD) M+171.

1. customthe temperature of the reaction near 5° C
2. additionOnce the addition
3. temperatureThe reaction was then cooled below 10° C.
4. customThe tetrahydrofuran was removed by evaporation under reduced pressure
5. additionthe resulting cloudy mixture was diluted with about 200 mL of water
6. extractionThis mixture was extracted three times with diethyl ether
7. washThe combined extracts were washed with water, twice with 10% aqueous sodium bicarbonate
8. dry with materialThe combined extracts were then dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-43c4bf9957714bdfbe0f008f39886823

Source dataset

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05914405