Water → 4-(3,5-Difluorophenyl)-1-butene
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]=1Participants
4
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
- extractionThis was extracted with 800 ml of hexane
- washwashed twice with saturated brine
- dry with materialdried with anhydrous sodium sulfate
- customAfter evaporation of the solvent
- 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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