Water → 3,4-Difluoro-1-(2-methoxyethoxy)benzene

HRID 1728040Notes

Reaction equation

HRID 1728040 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[H-].[Na+].Br[CH2:13][CH2:14][O:15][CH3:16].O>CN(C)C=O>[F:8][C:7]1[CH:6]=[CH:5][C:4]([O:9][CH2:13][CH2:14][O:15][CH3:16])=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 759273,4-DifluorophenolHCID 809722-Bromoethyl methyl ether

Product 1

HCID 574290663,4-Difluoro-1-(2-methoxyethoxy)benzeneYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-difluoro-phenol (10 g, 76.9 mmol) (Aldrich) in N,N-dimethylformamide (100 mL) was added sodium hydride (4.6 g, 115 mmol) and 1-bromo-2-methoxy-ethane (12.8 g, 92.2 mmol) (Aldrich). The reaction mixture was stirred at room temperature for 2 h, then heated at 80 ° C. for 16 h. The reaction mixture was cooled to room temperature and poured into water, extracted with ethyl acetate. The organic layers were combined, washed with water, brine, dried over dried over MgSO4, filtered and concentrated. The residue was purified with chromatography (EtOAc:Hexane=1:10) to give 1,2-difluoro-4-(2-methoxy-ethoxy)-benzene as colorless oil (Yield 6.3 g, 44%).

Workup

  1. temperatureheated at 80 ° C. for 16 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washwashed with water, brine
  5. customdried
  6. dry with materialover dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified with chromatography (EtOAc:Hexane=1:10)

Sources & evidence

ORD record
ord-c929d55c7fd64237a7e34378f1620719
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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