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

HRID 518000Notes

Reaction equation

HRID 518000 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][OH:22]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:20][CH2:21][OH:22])=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:3]=1

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Bromo-2-(trifluoromethyl)phenol (83 mmol, 20 g), potassium carbonate (166 mmol, 22.94 g) and 2-bromoethanol (124 mmol, 8.79 mL, 15.56 g) were combined and heated to reflux for overnight in Acetonitrile (200 mL). The reaction mixture was washed with water, 0.5M NaOH, dried over sodium sulfate and concentrated in vacuo. The resulting residue was taken up in hot heptane (300 mL) and allowed to crystallise. The solid was filtered off to afford 2-(4-bromo-2-(trifluoromethyl)-phenoxy)ethanol. (20.74 g)

Workup

  1. temperatureheated
  2. washThe reaction mixture was washed with water, 0.5M NaOH
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto crystallise
  6. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-5de1fadde5dc471da8087ce9ea939a0e
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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