Water → 2-Bromo-1-ethoxy-4-fluorobenzene

HRID 1266696Notes

Reaction equation

HRID 1266696 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].[CH2:16](I)[CH3:17].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 6054722-Bromo-4-fluorophenol

Product 1

HCID 106326422-Bromo-1-ethoxy-4-fluorobenzeneYield 101.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-4-fluorophenol (25.8 g) in DMF (100 ml) was added K2CO3 (20.5 g) and ethyl iodide (23.2 g). The mixture was stirred for 24 h at room temperature. Water (400 ml) was added and the mixture was extracted with hexane. The organic phase was washed with water, dried, filtered over a plug of silica gel and evaporated to yield 30.1 g of 2-bromo-1-ethoxy-4-fluoro-benzene as a colorless oil. MS: 220 ([M+H]+).

Workup

  1. extractionthe mixture was extracted with hexane
  2. washThe organic phase was washed with water
  3. customdried
  4. filtrationfiltered over a plug of silica gel
  5. customevaporated

Sources & evidence

ORD record
ord-67daadaee3e2432d9d30fcad7165206d
Source dataset
uspto-grants-2003_04
Patent number
US06548694B2

Reaction notes

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