Carbon tetrabromide → HCID 18700174, compound

To a stirred solution of 2-(2,2,2-trifluoroethoxy)-4-fluorobenzyl alcohol (1.2 g, 5.3 mmol) from Step 2 above in ether (30 mL) was added CBr4 (3.0 g, 9.2 mmol) and triphenylphosphine (2.4 g, 9.2 mmol). The mixture was stirred at ambient temperature for 14 h. Triphenylphosphine oxide was removed by filtration and the filtrate was diluted with EtOAc (50 mL) and washed with saturated aqueous NaHCO3 (2×50 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressureized silica gel column chromatography using a gradient elution of 0-5% EtOAc:hexanes to give 2-(2,2,2-trifluoroethoxy)-4-fluorobenzyl bromide as a colorless oil (HPLC retention time=10.4 min (method A)).

1. customTriphenylphosphine oxide was removed by filtration
2. additionthe filtrate was diluted with EtOAc (50 mL)
3. washwashed with saturated aqueous NaHCO3 (2×50 mL)
4. dry with materialThe organic phase was dried (MgSO4)
5. filtrationfiltered
6. customthe solvent was removed under reduced pressure
7. customThe residue was purified by pressureized silica gel column chromatography
8. washa gradient elution of 0-5% EtOAc

ORD record

ord-ee2a21e0e6e44a9cbfea1c553354283f

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05968938