Thionyl Chloride → HCID 59824802, compound

HRID 1916967Notes

Reaction equation

HRID 1916967 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH2:18][CH2:19][CH3:20])=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O>CN(C=O)C>[Cl:24][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[N:9]1[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58433795HCID 58433795, compound

Product 1

HCID 59824802HCID 59824802, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Distilled THF (20 mL) was added to 3-(4-fluorophenyl)-3-hydroxy-2-propyl-2,3-dihydroisoindol-1-one (200 mg, 0.7 mmol) followed by thionyl chloride (0.06 mL, 0.84 mmol) and a catalytic amount of DMF (3 drops). The mixture was stirred at room temperature under nitrogen for 4 h and monitored by TLC. Removal of the solvent under vacuum gave 3-chloro-3-(4-fluorophenyl)-2-propyl-2,3-dihydroisoindol-1-one as a colourless oil (212 mg, 0.69 mmol, 100%) which was used immediately without further purification.

Workup

  1. distillationDistilled THF (20 mL)
  2. customRemoval of the solvent under vacuum

Sources & evidence

ORD record
ord-cb75accaf5ca42e292c1880970b6f27e
Source dataset
uspto-grants-2013_12
Patent number
US08618158B2

Reaction notes

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