Thionyl Chloride → HCID 58950926, compound

HRID 533916Notes

Reaction equation

HRID 533916 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][C:11]([OH:13])=O)=[C:4]([F:14])[CH:3]=1.O=S(Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[C:7]([CH3:8])=[C:6]2[C:5]([CH2:9][CH2:10][C:11]2=[O:13])=[C:4]([F:14])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58950904HCID 58950904, compound

Product 1

HCID 58950926HCID 58950926, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-bromo-2-fluoro-5-methylphenyl)propanoic acid (EP1795524 A1; 8.4 g) in DCM (200 mL) was added SOCl2 (19.1 g) dropwise at r.t. The mixture was stirred for 2 hours at r.t. The solvent was removed under reduced pressure. AlCl3 (21.4 g) was added to the residue. The brown slurry was heated to 130° C. for 1.5 hours and then cooled to r.t. The residue was dissolved in EA (300 mL) and then washed with water and brine. The organic phase was dried over Na2SO4. The residue obtained after filtration and evaporation was purified by SGC (PE/EA 400:1) to provide the title compound. MS ESI+: m/z=243 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionAlCl3 (21.4 g) was added to the residue
  3. temperatureThe brown slurry was heated to 130° C. for 1.5 hours
  4. temperaturecooled to r.t
  5. dissolutionThe residue was dissolved in EA (300 mL)
  6. washwashed with water and brine
  7. dry with materialThe organic phase was dried over Na2SO4
  8. customThe residue obtained
  9. filtrationafter filtration and evaporation
  10. customwas purified by SGC (PE/EA 400:1)

Sources & evidence

ORD record
ord-9ac66c7ba4c44e8b8db606e0e223d087
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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