Methyl Ethyl Ketone → 1,3-Dibromo-2-(2-chloroethoxy)-5-fluorobenzene

HRID 399010Notes

Reaction equation

HRID 399010 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Br:9])[C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][Cl:20].CC(=O)CC>C(OCC)C>[Cl:20][CH2:19][CH2:18][O:10][C:3]1[C:2]([Br:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=1[Br:9]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 676542,6-Dibromo-4-fluorophenol

Product 1

HCID 108304061,3-Dibromo-2-(2-chloroethoxy)-5-fluorobenzeneYield 99.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2,6-dibromo-4-fluoro-phenol (55 g, 0.20 mol), potassium carbonate (60 g, 0.43 mol), 1-bromo-2-chloroethane (32.5 g, 0.23 mol) and 2-butanone (500 mL) was heated to reflux for 2 hours and allowed to cool to ambient temperature. The solids were filtered and the solvent was removed under vacuum to afford an oil. The oil was dissolved in diethyl ether (300 mL) and washed with water, dried over anhydrous magnesium sulfate, charcoalized, and filtered through Solka floc to afford 65.9 g (97.2%) of an oil; MS EI m/e 330/332/334/336 (M+ ; 1H NMR (CDCl3) δ 3.89 (2H, t, J=6.1 Hz), 4.23 (2H, t, J=6.1 Hz), 7.28 (2H, d, J=7.5 Hz).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. filtrationThe solids were filtered
  4. customthe solvent was removed under vacuum
  5. customto afford an oil
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered through Solka floc

Sources & evidence

ORD record
ord-1a72ba867804443a92f5ceca73991469
Source dataset
uspto-grants-1998_10
Patent number
US05817690

Reaction notes

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