Ethyl Bromide → 4-Bromo-1-ethoxy-2-fluorobenzene

HRID 2052770Notes

Reaction equation

HRID 2052770 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[CH2:10](Br)[CH3:11].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH3:11])=[C:4]([F:9])[CH:3]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 145169324-Bromo-1-ethoxy-2-fluorobenzeneYield 99.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

100 g (0.524 mol) of 4-bromo-2-fluorophenol and 66.7 g (0.612 mol) of ethyl bromide were dissolved in 2 1 of ethyl methyl ketone and refluxed for 24 hours in the presence of 185 g (1.34 mol) of potassium carbonate. The solution was subsequently filtered, the filtrate was evaporated, and the crude product was filtered through silica gel with n-hexane, giving 114 g (99% of theory) of 4-bromo-1-ethoxy-2-fluorobenzene as a colourless liquid.

Workup

  1. filtrationThe solution was subsequently filtered
  2. customthe filtrate was evaporated
  3. filtrationthe crude product was filtered through silica gel with n-hexane

Sources & evidence

ORD record
ord-4ede4f53ddc1451e8c47f745efbf5c8e
Source dataset
uspto-grants-2008_02
Patent number
US07326447B2

Reaction notes

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