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

HRID 1595127Notes

Reaction equation

HRID 1595127 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-027fd5aee3984d3798dd6e3f5a2faad6
Source dataset
uspto-grants-2001_09
Patent number
US06287646B1

Reaction notes

Loading…