Sulfuric Acid → 2-(2-Chloro-6-fluorophenyl)-propene

HRID 343024Notes

Reaction equation

HRID 343024 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9](O)([CH3:11])[CH3:10].S(=O)(=O)(O)O>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([CH3:11])=[CH2:10]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 540290942-(2-Chloro-6-fluorophenyl)propan-2-ol

Product 1

HCID 543491142-(2-Chloro-6-fluorophenyl)-propeneYield 67.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2-chloro-6-fluorophenyl)propan-2-ol (19.0 g), concentrated sulphuric acid and water was heated at reflux for 2 hours. It was cooled and extracted with ether, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography eluted with hexane to give 2-(2-chloro-6-fluorophenyl)-propene (11.6 g) as a clear oil, NMR (CDCl3) 1.95(s,3H) 4.95(s,1H), 5.85(s,1H), 6.85-7.0(m,1H), 7.05-7.2(m,2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureIt was cooled
  4. extractionextracted with ether
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by chromatography
  10. washeluted with hexane

Sources & evidence

ORD record
ord-d793c2a2e7fd45a1bccbeba3696812d1
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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