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

HRID 266580

Reaction equation

HRID 266580 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-a507d08a3b8841fd851649d7b150fc81
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Linked notes

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