Water → 2-Chloro-4-fluoro-1-(2-methoxyethoxy)benzene

HRID 253442Notes

Reaction equation

HRID 253442 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].Br[CH2:11][CH2:12][O:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:11][CH2:12][O:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 748142-Chloro-4-fluorophenolHCID 809722-Bromoethyl methyl ether

Product 1

HCID 178216442-Chloro-4-fluoro-1-(2-methoxyethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 2-chloro-4-fluorophenol (52, 2.40 mL, 0.0213 mol) in N,N-dimethylformamide (30.0 mL), 1-bromo-2-methoxy-ethane (2.00 mL, 0.0213 mol) and potassium carbonate (3.00 g, 0.0217 mol) were added under an atmosphere of nitrogen. The reaction was stirred at 80° C. for 2 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a colorless oil (122, 1.50 g, 34.4%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate in hexane
  7. customto give a colorless oil (122, 1.50 g, 34.4%)

Sources & evidence

ORD record
ord-cfef74b3fe5b47b09c57ad6d336bf34b
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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