Acetonitrile → 1-Bromo-4-ethoxy-2-(trifluoromethyl)benzene

HRID 2246426Notes

Reaction equation

HRID 2246426 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].C(=O)([O-])[O-].[K+].[K+].[C:19](#N)[CH3:20]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:19][CH3:20])=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 222773074-Bromo-3-(trifluoromethyl)phenol

Product 1

HCID 220349931-Bromo-4-ethoxy-2-(trifluoromethyl)benzene

Procedure

A stirred suspension of 4-bromo-3-trifluoromethyl-phenol (117.6 g, 0.49 mol) iodoethane (77.6 g, 0.49 mol) and potassium carbonate (101.2 g, 0.73 mol) in acetonitrile (600 ml) was heated to reflux for 2.5 hours. The mixture was concentrated under reduced pressure before partitioning between dichloromethane (1 litre) and water (1 litre). The organic phase was collected and dried over magnesium sulfate before concentration under reduced pressure to afford 4-bromo-1-ethoxy-3-trifluoromethyl-benzene (126.97 g). 1H NMR (CDCl3): δ 7.66 (s, 1H) 7.56 (d, 1H) 6.86 (s, 1H) 4.09 (q, 2H) 1.44 (t, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custombefore partitioning between dichloromethane (1 litre) and water (1 litre)
  5. customThe organic phase was collected
  6. dry with materialdried over magnesium sulfate before concentration under reduced pressure

Sources & evidence

ORD record
ord-f1abf76c8abe4cd2957470c9ff719c6b
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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