Water → 1-[4-(Benzyloxy)butoxy]-4-fluorobenzene

HRID 384450Notes

Reaction equation

HRID 384450 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 4422181((4-Bromobutoxy)methyl)benzene

Product 1

HCID 595275161-[4-(Benzyloxy)butoxy]-4-fluorobenzeneYield 69.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluorophenol (500 mg) and benzyl 4-bromobutyl ether (1.1 g) were dissolved in DMF (20 mL), and potassium carbonate (1.0 g) was added thereto at room temperature, followed by stirring at 100° C. for 18 hours. The reaction mixture was allowed to cool to room temperature, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=90/10) to obtain 1-[4-(benzyloxy)butoxy]-4-fluorobenzene (851 mg).

Workup

  1. customat room temperature
  2. temperatureto cool to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed sequentially with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=90/10)

Sources & evidence

ORD record
ord-52a0c517beb1424fa6d9f0db3c9eb3c7
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

Loading…