Water → 1-(But-3-en-1-yl)-3,5-difluorobenzene

HRID 2121095Notes

Reaction equation

HRID 2121095 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5]Br.O.[CH2:12]1[CH2:16]OC[CH2:13]1>>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][CH2:16][CH:12]=[CH2:13])[CH:7]=[C:8]([F:10])[CH:9]=1

Participants

4

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 5188963,5-Difluorobenzyl bromide

Product 1

HCID 234370931-(But-3-en-1-yl)-3,5-difluorobenzene

Procedure

A 176 g portion of 3,5-difluorobenzyl bromide was dissolved in 300 ml of THF to which was subsequently added dropwise 450 ml of allyl magnesium chloride THF solution (2 mol/l) at room temperature. This was stirred for 1 hour and then mixed with 300 ml of water. This was extracted with 800 ml of hexane, washed twice with saturated brine and then dried with anhydrous sodium sulfate. After evaporation of the solvent, the resulting residue was distilled (79-82° C./20 mmHg) to obtain 104 g of 3,5-difluoro-1-(3-butenyl)benzene.

Workup

  1. extractionThis was extracted with 800 ml of hexane
  2. washwashed twice with saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customAfter evaporation of the solvent
  5. distillationthe resulting residue was distilled (79-82° C./20 mmHg)

Sources & evidence

ORD record
ord-c0ca80a6bb1844c0932c5bdc78c151f7
Source dataset
uspto-grants-2004_02
Patent number
US06693223B1

Reaction notes

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