2-Bromophenol → 1-Bromo-2-(2,2,2-trifluoroethoxy)benzene

HRID 842793Notes

Reaction equation

HRID 842793 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[F:9][C:10]([F:14])([F:13])[CH2:11]I.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:11][C:10]([F:14])([F:13])[F:9]

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethane

Product 1

HCID 226154791-Bromo-2-(2,2,2-trifluoroethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-bromophenol (5.89 g, 34.0 mmol) and 2,2,2-trifluoroethyliodide (16.8 g, 80.0 mmol) in DMF (60 mL) was treated with potassium carbonate (24.1 g, 174 mmol) at room temperature. The resulting mixture was heated in an oil bath (60° C., 2 d). The solvent was removed in vacuo and the residue dissolved in ether and water. The aqueous layer was extracted with two additional portions of ether and the combined organic extracts were washed with three portions of 1M NaOH solution and dried over Na2SO4. The solvent was removed in vacuo to afford the title compound (50).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in ether
  3. extractionThe aqueous layer was extracted with two additional portions of ether
  4. washthe combined organic extracts were washed with three portions of 1M NaOH solution
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-893b3b0a4170404fb0624e665c320a23
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

Loading…