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

HRID 1858365Notes

Reaction equation

HRID 1858365 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 silica gel to afford 65.9 g (97.2%) of product as an oil; MS EI m/e 330/332/334/336 (M+); 1H NMR (CDCl3) δ3.89 (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 silica gel

Sources & evidence

ORD record
ord-854c1a890d97427098e9e63fc28deb43
Source dataset
uspto-grants-2000_11
Patent number
US06150533

Reaction notes

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