Borane → (4-Bromo-3-fluorophenyl)methanol

To a solution of the product from Step H (14.69 g, 67.0 mmol) in 40 mL of tetrahydrofuran at 0° C. was added borane in THF (141 mL, 141 mmol, 1M) dropwise, keeping the reaction temperature below 5° C. The solution was allowed to warm to room temperature, then stirred for one hour. The reaction was cautiously quenched at 0° C. with 50 mL of water, concentrated in vacuo, and partitioned between EtOAc and water. The aqueous layer was extracted twice with EtOAc, and the combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled product.

1. customthe reaction temperature below 5° C
2. customThe reaction was cautiously quenched at 0° C. with 50 mL of water
3. concentrationconcentrated in vacuo
4. custompartitioned between EtOAc and water
5. extractionThe aqueous layer was extracted twice with EtOAc
6. washthe combined organic layers were washed with brine
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-cb57dfdbe1af44cbbc38875cc3ab9f74

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06562823B1