Water → 3-(3,5-Difluorophenyl)-1-propene

HRID 1995689Notes

Reaction equation

HRID 1995689 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[F:5][C:6]1[CH:7]=[C:8](Br)[CH:9]=[C:10]([F:12])[CH:11]=1.[Mg].O>O1CCCC1>[CH2:3]([C:8]1[CH:7]=[C:6]([F:5])[CH:11]=[C:10]([F:12])[CH:9]=1)[CH:2]=[CH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 1363131-Bromo-3,5-difluorobenzeneHCID 5462224Magnesium

Product 1

HCID 27583443-(3,5-Difluorophenyl)-1-propene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of allyl bromide (2.5 g) in dry tetrahydorfuran (10 ml) was added dropwise with stirring to 3,5-difluorobromobenzene (4.0 g) with magnesium (0.5 g) in dry tetrahydrofuran) in dry tetrahydrofuran (40 ml), whilst maintaining the temperature of the mixture at about 20° C. When the addition was complete the mixture was allowed to warm to the ambient temperature (ca. 25° C.) After a period of 18 hours the mixture was poured into water (100 ml) and the resultant mixture extracted with diethyl ether, the extract washed with water, dried over anhydrous magnesium sulphate and the ether removed by distillation at atmospheric pressure. The residual oil was purified by distillation at atmospheric pressure to yield allyl-3,5-difluorobenzene (b.p. 154-155°) as a colourless oil.

Workup

  1. additionWhen the addition
  2. temperatureto warm to the ambient temperature (ca. 25° C.) After a period of 18 hours the mixture
  3. extractionthe resultant mixture extracted with diethyl ether
  4. washthe extract washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customthe ether removed by distillation at atmospheric pressure
  7. distillationThe residual oil was purified by distillation at atmospheric pressure

Sources & evidence

ORD record
ord-c171fe693bb8473fa17cf85cb264ebbb
Source dataset
uspto-grants-1983_09
Patent number
US04405640

Reaction notes

Loading…