2-Bromoethanol → 2-(4-Bromo-2-(trifluoromethyl)phenoxy)-ethanol

HRID 912510Notes

Reaction equation

HRID 912510 reaction equation
Br[CH2:2][CH2:3][OH:4].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:2][CH2:3][OH:4])=[C:8]([C:13]([F:14])([F:15])[F:16])[CH:7]=1

Participants

6

Reactant 3

HCID 108982-Bromoethanol2×HCID 11430Potassium CarbonateHCID 142784o-Cresol, 4-bromo-alpha,alpha,alpha-trifluoro-

Product 1

HCID 576575832-(4-Bromo-2-(trifluoromethyl)phenoxy)-ethanol

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromoethanol (23.3 g) was added to a mixture of 4-bromo-2-(trifluoromethyl)-phenol (30 g) and potassium carbonate (34.4 g) in acetonitrile (200 ml). The above mixture was refluxed for 8 hours then another portion of 2-bromoethanol (8 g) was added and the reflux continued for another 6 hours. After diluting with ethyl acetate (500 ml), the mixture was washed with water (300 ml) then 0.1 M sodium hydroxide (200 ml). Organic layer was dried over magnesium sulphate, solvent removed under reduced pressure, the residue was taken into heptane by heat, 2-(4-bromo-2-(trifluoromethyl)-phenoxy)-ethanol crystalised and collected by filtration (17 g).

Workup

  1. temperatureThe above mixture was refluxed for 8 hours
  2. washthe mixture was washed with water (300 ml)
  3. dry with materialOrganic layer was dried over magnesium sulphate, solvent
  4. customremoved under reduced pressure
  5. temperatureby heat
  6. custom2-(4-bromo-2-(trifluoromethyl)-phenoxy)-ethanol crystalised
  7. filtrationcollected by filtration (17 g)

Sources & evidence

ORD record
ord-3f384afd90ea40d9bad3290b78328376
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

Loading…