Sodium Hydroxide → HCID 86718605, compound

2-Methoxyethoxymethylchloride (0.67 mL, 5.83 mmol) was added dropwise to a solution of 3-bromo-3′-fluoro-[1,1′-biphenyl]-4-ol (˜5.55 mmol) and diisopropylethylamine (1.93 mL, 11.1 mmol) in dry dichloromethane (20 mL) at room temperature under nitrogen. The reaction mixture was stirred at room temperature under nitrogen for 3 days, 1.0 M aqueous sodium hydroxide (20 mL) added and the biphasic mixture stirred vigorously for 20 minutes. The reaction mixture was partitioned between ethyl acetate (100 mL) and 1.0 M aqueous sodium hydroxide solution (100 mL), the organic phase separated, washed with water (75 mL) and saturated brine (75 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 10% ethyl acetate (containing 2% methanol) in hexanes to give 3-bromo-3′-fluoro-4-((2-methoxyethoxy)methoxy)-1,1′-biphenyl (1.57 g, 80% yield) as a colorless oil.

1. stirringthe biphasic mixture stirred vigorously for 20 minutes
2. customThe reaction mixture was partitioned between ethyl acetate (100 mL) and 1.0 M aqueous sodium hydroxide solution (100 mL)
3. customthe organic phase separated
4. washwashed with water (75 mL) and saturated brine (75 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 10% ethyl acetate (containing 2% methanol) in hexanes

ORD record

ord-2a2fadd40a6d48f699bd9ab131f89d19

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409893B2