Thionyl Chloride → HCID 14770843, compound

HRID 1651571Notes

Reaction equation

HRID 1651571 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:13][CH2:12][CH:11](O)[CH2:10]2)=[C:4]([F:15])[CH:3]=1.S(Cl)([Cl:18])=O>>[Br:1][C:2]1[CH:3]=[C:4]([F:15])[C:5]([CH:9]2[CH2:13][CH2:12][CH:11]([Cl:18])[CH2:10]2)=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 14770844HCID 14770844, compound

Product 1

HCID 14770843HCID 14770843, compound

Procedure

A solution of 27.7 g (0.1 mol) of 3-(4-bromo-2,5-difluorophenyl)cyclopentanol in 150 ml of thionyl chloride was heated at reflux until gas evolution ceased (4 hours). The solvent was removed in vacuo and the residue was triturated with toluene (2×200 ml) which was also removed in vacuo. The residue was dissolved in ether, washed with water (3×100 ml), dried (MgSO4), filtered, and evaporated in vacuo to give 26.2 g of the title compound which was used without further purification.

Workup

  1. temperatureat reflux until gas evolution
  2. custom(4 hours)
  3. customThe solvent was removed in vacuo
  4. customthe residue was triturated with toluene (2×200 ml) which
  5. customwas also removed in vacuo
  6. dissolutionThe residue was dissolved in ether
  7. washwashed with water (3×100 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-1bfc5690bf94406dba3109908e95ddcf
Source dataset
uspto-grants-1990_05
Patent number
US04929613

Reaction notes

Loading…