Thionyl Chloride → 4,6-difluoro-2,3-dihydro-1H-inden-1-one

HRID 130608Notes

Reaction equation

HRID 130608 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[CH2:13][CH2:14][C:15]([OH:17])=O>C(Cl)Cl>[F:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:7]=1[CH2:13][CH2:14][C:15]2=[O:17]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 49863953-(2,4-difluorophenyl)propanoic Acid

Product 1

HCID 109539204,6-difluoro-2,3-dihydro-1H-inden-1-oneYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (54.6 g) was added dropwise at 40° C. to a solution of 3-(2,4-di-fluorophenyl)propionic acid (57 g) in methylene chloride (200 ml). After reaction was complete, excess thionyl chloride and the solvent were removed by distillation. The oily residue was added dropwise at 40° C. to a suspension of aluminium chloride (88.5 g) in methylene chloride (200 ml). The reaction mixture was added to dilute hydrochloric acid after 18 hours at 40° C. The aqueous phase was separated off and extracted once with methylene chloride (250 ml). The combined organic phases were freed from the solvent and then distilled in vacuo. 41 g of a colorless solid were obtained (m.p.: 103° C.).

Workup

  1. customAfter reaction
  2. customexcess thionyl chloride and the solvent were removed by distillation
  3. additionThe oily residue was added dropwise at 40° C. to a suspension of aluminium chloride (88.5 g) in methylene chloride (200 ml)
  4. additionThe reaction mixture was added to dilute hydrochloric acid after 18 hours at 40° C
  5. customThe aqueous phase was separated off
  6. extractionextracted once with methylene chloride (250 ml)
  7. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-ce96f0bca0d94819984a1563fec5f0b3
Source dataset
uspto-grants-2008_06
Patent number
US07381832B2

Reaction notes

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