Bromine → HCID 86718606, compound

A solution of bromine (887 mg, 5.55 mmol) in dichloromethane (10 mL) was added dropwise to a solution of 4-(3-fluorophenyl)phenol [purchased from Combi-Blocks] (1.044 g, 5.55 mmol) in dichloromethane (10 mL) and acetonitrile (5 mL) at 0° C. under nitrogen. The reaction mixture was then stirred at 0° C. to room temperature for 17 hours. The reaction mixture was partitioned between ethyl acetate (100 mL) and saturated aqueous sodium hydrogen carbonate solution (100 mL) containing 10% aqueous sodium thiosulfate solution (10 mL). The organic phase was separated, washed with water (100 mL) and saturated brine (100 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give an orange oil. The crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 15% ethyl acetate (containing 2% methanol) in hexanes to give 3-bromo-3′-fluoro-[1,1′-biphenyl]-4-ol (1.56 g, quant.) as a colorless oil.

1. customThe reaction mixture was partitioned between ethyl acetate (100 mL) and saturated aqueous sodium hydrogen carbonate solution (100 mL)
2. additioncontaining 10% aqueous sodium thiosulfate solution (10 mL)
3. customThe organic phase was separated
4. washwashed with water (100 mL) and saturated brine (100 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto give an orange oil
9. customThe crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 15% ethyl acetate (containing 2% methanol) in hexanes

ORD record

ord-199ba0f50d16474f8faf34e7cf9e32d0

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409893B2