Benzyl Bromide → 4-Benzyloxy-5-(4-fluorophenoxy)-1-pentene

HRID 867096Notes

Reaction equation

HRID 867096 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][CH:8]([OH:12])[CH2:9][CH:10]=[CH2:11])=[CH:4][CH:3]=1.CCCCCC.[H-].[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[CH2:23]([O:12][CH:8]([CH2:7][O:6][C:5]1[CH:13]=[CH:14][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][CH:10]=[CH2:11])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 24758Sodium hydrideHCID 213175735-(4-Fluorophenoxy)-1-penten-4-ol

Product 1

HCID 213176584-Benzyloxy-5-(4-fluorophenoxy)-1-pentene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

A solution of 5-(4-fluorophenoxy)-1-penten-4-ol (9.81 g., 0.05 mole) in dry dimethylformamide (15 ml.) is added dropwise to a stirred suspension of hexane (2 × 10 ml.)--prewashed sodium hydride (50% dispersion in mineral oil, 2.64 g., 0.055 mole) in dry dimethylformamide (45 ml.) at 25° C. Upon cessation of gas evolution, the reaction mixture is cooled to 0°-5° C. and treated with a solution of benzyl bromide (10.3 g., 0.06 mole) in dry dimethylformamide (10 ml.). The resulting mixture is stirred at 25° C. for 16 hours, then heated at 100° C. for 1 hour. After cooling to 25° C., the reaction mixture is diluted with ice water (50 ml.) and extracted with ether four times. The combined organic extract is washed with 2 N hydrochloric acid and saturated aqueous brine, dried over magnesium sulfate and filtered. In vacuo evaporation of the filtrate leaves an oily residue which affords the title compound upon distillation as a colorless oil (13.1 g., 92%), bp0.025 112°-116° C.; pmr (CCl4) δ2.37 (2H, t), 3.5-4.0 (3H, m), 4.57 (2H, s), 4.8-5.05 (H, m), 5.05-5.25 (H, m), 5.4-6.2 (H, m), 6.6-7.1 (4H, m) and 7.19 (5H, s).

Workup

  1. customat 25° C
  2. temperatureUpon cessation of gas evolution, the reaction mixture is cooled to 0°-5° C.
  3. temperatureheated at 100° C. for 1 hour
  4. temperatureAfter cooling to 25° C.
  5. extractionextracted with ether four times
  6. extractionThe combined organic extract
  7. washis washed with 2 N hydrochloric acid and saturated aqueous brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customIn vacuo evaporation of the filtrate
  11. customleaves an oily residue which

Sources & evidence

ORD record
ord-2b9ed2ca36b14e29a8b280b667b0512f
Source dataset
uspto-grants-1978_07
Patent number
US04102888

Reaction notes

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