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

HRID 517991Notes

Reaction equation

HRID 517991 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.O.[OH-].[Na+]>[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

8

Reactant 3

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

Product 1

HCID 576575832-(4-Bromo-2-(trifluoromethyl)phenoxy)-ethanolYield 80.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Bromoethanol (10.37 g) was added to a mixture of 4-bromo-2-(trifluoro-methyl)phenol (20 g) and potassium carbonate (22.94 g) in Acetonitrile (150 ml). The above reaction mixture was refluxed overnight, then diluted with ethyl acetate (500 ml), water (300 ml) the 0.5M sodium hydroxide (300 ml). Organic layer was separated and dried over magnesium sulphate, solvent removed under reduced pressure to give white solid (19 g), NMR consistent with product. 1H NMR (CDCl3) δ: 7.69 (d, 1H), 7.58 (dd, 1H), 6.91 (d, 1H), 4.15 (t, 2H), 3.97 (t, 2H).

Workup

  1. customThe above reaction mixture
  2. temperaturewas refluxed overnight
  3. customOrganic layer was separated
  4. dry with materialdried over magnesium sulphate, solvent
  5. customremoved under reduced pressure

Sources & evidence

ORD record
ord-2a390911041d4fb0aaacc39f28bb69f3
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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