Sodium hydride → HCID 70816855, compound

To a stirred solution of (4-bromo-2-fluorophenyl)methanol (5 g, 24.509 mmol) in DMF (50 mL) at 0° C. NaH (60% suspension in mineral oil, 1.96 g, 49.018 mmol) was added in portions. To the resulting suspension ((2-bromoethoxy)methyl)benzene (6.32 g, 29.41 mmol) was added at 0° C., and the reaction mixture was allowed to stir at RT for 16 h until complete consumption of (4-bromo-2-fluorophenyl)methanol, as evidenced by TLC analysis. The reaction mixture was quenched with MeOH (5 mL), diluted with ice cold water (50 mL) and was extracted with EtOAc (3×100 mL). The combined EtOAc layer was washed with water (50 mL), brine (50 mL), dried over anhydrous NaSO4, filtered and concentrated. The obtained crude compound was purified by CC using 5% EtOAc in PE as eluent to afford 1-((2-(benzyloxy)ethoxy)methyl)-4-bromo-2-fluorobenzene (4.2 g, 51%) as yellow liquid (TLC solvent system: 30% EtOAc in PE; Rf: 0.6).

1. customat 0° C
2. customThe reaction mixture was quenched with MeOH (5 mL)
3. additiondiluted with ice cold water (50 mL)
4. extractionwas extracted with EtOAc (3×100 mL)
5. washThe combined EtOAc layer was washed with water (50 mL), brine (50 mL)
6. dry with materialdried over anhydrous NaSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe obtained crude compound
10. customwas purified by CC

ORD record

ord-ed3409a41719491db26d794b5093e682

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946204B2