4-Fluorophenol → 1-(2,2-Diethoxyethoxy)-4-fluorobenzene

HRID 503140Notes

Reaction equation

HRID 503140 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[CH2:13]Br)[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[CH2:13][O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:10]

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 114475181-(2,2-Diethoxyethoxy)-4-fluorobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 10.0 g of 4-fluorophenol and 16.1 ml of bromoacetaldehyde diethylacetal in 100 ml dimethylformaldehyde was added 18.5 g of potassium carbonate at room temperature, and the mixture was stirred at 120° C. for two days. The reaction mixture was filtered through Celite, and the filtrate was diluted with ethyl acetate. The organic layer was sequentially washed with saturated aqueous ammonium chloride solution and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=0:10 to 1:20), to give 17.3 g of the title compound as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. additionthe filtrate was diluted with ethyl acetate
  3. washThe organic layer was sequentially washed with saturated aqueous ammonium chloride solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe crude product was purified
  7. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=0:10 to 1:20)

Sources & evidence

ORD record
ord-9b798ee227b84dec8d4c1654f51162f5
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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