Allyl Alcohol → 1-Allyloxy-3-bromo-5-fluorobenzene

HRID 272277Notes

Reaction equation

HRID 272277 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].[H-].[Na+].[F:7][C:8]1[CH:9]=[C:10]([Br:15])[CH:11]=[C:12](F)[CH:13]=1>CC(N(C)C)=O>[CH2:1]([O:4][C:12]1[CH:13]=[C:8]([F:7])[CH:9]=[C:10]([Br:15])[CH:11]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 1363131-Bromo-3,5-difluorobenzene

Product 1

HCID 220465701-Allyloxy-3-bromo-5-fluorobenzeneYield 69.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a DMA (400 ml) solution of allyl alcohol (8.9 g, 0.154 mol), at room temperature (r.t.) is added NaH (60% oil dispersion) (6.4 g, 0.160 mol) in portions. The mixture is stirred at r.t. for 1.5 h followed by the slow addition of 3,5-difluoro bromobenzene (17.9 ml, 30 g, 0.155 mol). The reaction mixture is stirred at r.t. overnight. The reaction is quenched by the addition of 1500 ml of water and extracted with ether (4×300 ml). The organic layer is dried over MgSO4 and concentrated at reduced pressure to yield 24.6 g (69%) of a colorless oil after flash chromatography (pentane, rf.=0.3). Anal. Calc. for C9H8BrFO: C, 46.78; H, 3.49. Found: C. 46.18, H, 3.45. Calculated mass for C9H8OFBr: 229.97. Mass found for C9H8OFBr: (OAMS) ES−: 189.0 (M-allyl)

Workup

  1. stirringThe reaction mixture is stirred at r.t. overnight
  2. customThe reaction is quenched by the addition of 1500 ml of water
  3. extractionextracted with ether (4×300 ml)
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-82403a9db12147acad1c4360621efead
Source dataset
uspto-grants-2008_11
Patent number
US07456163B2

Reaction notes

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