Borane;tetrahydrofuran → 3-(4-Bromophenyl)propan-1-ol

To a stirred solution of 3-(4-bromophenyl)propanoic acid (7 g, 30.56 mmol) in THF (50.9 ml) at −10° C. was added borane tetrahydrofuran complex (1M in THF) (153 ml, 152.79 mmol) dropwise over 1 h, keeping the temperature below 0° C. The reaction mixture was allowed to warm to RT overnight then cooled to 5° C. and quenched with MeOH (50 mL). Reaction mixture stirred at RT for 1 h and then concentrated to give an oil. The oil was partitioned between ether (120 mL) and 2M NaOH (60 mL). The organic layer was then washed with water (60 mL) and brine, dried over magnesium sulfate, filtered and evaporated to afford the sub-title compound. Yield: 6.17 g

1. customthe temperature below 0° C
2. temperaturethen cooled to 5° C.
3. customquenched with MeOH (50 mL)
4. customReaction mixture
5. concentrationconcentrated
6. customto give an oil
7. customThe oil was partitioned between ether (120 mL) and 2M NaOH (60 mL)
8. washThe organic layer was then washed with water (60 mL) and brine
9. dry with materialdried over magnesium sulfate
10. filtrationfiltered
11. customevaporated

ORD record

ord-2040f7368e0f4a8486fae23555cc9911

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273774B2