Allyl bromide → 2-[4-Fluorophenyl]ethyl allyl ether

HRID 265305

Reaction equation

HRID 265305 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:13](Br)[CH:14]=[CH2:15]>CN(C=O)C>[CH2:15]([O:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 820684-Fluorophenethyl Alcohol

Product 1

HCID 190822842-[4-Fluorophenyl]ethyl allyl etherYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[4-Fluorophenyl]ethanol (7.0 g) was added slowly to a stirred suspension of sodium hydride (1.25 g, 60% as dispersion in oil prewashed with petroleum ether bp 60°-80°) in DMF (50 ml). The mixture was stirred for 30 min at room temperature. Allyl bromide (6.0 g) was then added slowly and the whole allowed to stir overnight. The reaction was partitioned between water and ether. The aqueous layer was further extracted with ether and the combined ethereal extracts were washed with water and dried (MgSO4). The ether was removed under reduced pressure to yield the crude subtitled compound as a colourless oil (8.7 g, 96%).

Workup

  1. stirringto stir overnight
  2. customThe reaction was partitioned between water and ether
  3. extractionThe aqueous layer was further extracted with ether
  4. washthe combined ethereal extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. customThe ether was removed under reduced pressure

Sources & evidence

ORD record
ord-cf924c3311fe4226999a63b902a7d7f4
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Linked notes

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