Water → 4-Bromo-1-(2-ethoxyethoxy)-2-fluorobenzene

HRID 1978621Notes

Reaction equation

HRID 1978621 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][O:19][CH2:20][CH3:21].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH2:18][O:19][CH2:20][CH3:21])=[C:4]([F:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl ether2×HCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 219959004-Bromo-1-(2-ethoxyethoxy)-2-fluorobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-bromo-2-fluorophenol (10.07 g) and potassium carbonate (9.5 g) in DMF (100 ml) was added at room temperature 2-bromoethylethyl ether (6.0 ml), and the mixture was stirred for 18 hours. To the mixture was added 2-bromoethylethyl ether (1.2 ml), and the mixture was stirred at 55° C. for 5 hours. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water (thrice) and saturated brine (once), and dried with magnesium sulfate. The solvent was evaporated under reduced pressure to give pale yellow oil of 4-bromo-1-(2-ethoxyethoxy)-2-fluorobenzene (13.79 g).

Workup

  1. stirringthe mixture was stirred at 55° C. for 5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water (thrice) and saturated brine (once), and
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2097295c9fa2417a86795caf6889427d
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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