Trifluoroacetic acid → 3,4-Dichloro-2-fluorophenol

HRID 252162

Reaction equation

HRID 252162 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([F:16])=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1.[Cl:17]N1C(=O)CCC1=O>C(#N)C>[Cl:8][C:9]1[C:10]([F:16])=[C:11]([OH:15])[CH:12]=[CH:13][C:14]=1[Cl:17]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 31398ChlorosuccinimideHCID 27737123-Chloro-2-fluorophenol

Product 1

HCID 212741443,4-Dichloro-2-fluorophenolYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added to a solution of 3-chloro-2-fluorophenol (750 mg, 5.12 mmol) and N-chlorosuccinimide (684 mg, 5.12 mmol) in acetonitrile (30 mL) and the reaction mixture stirred for 24 h. The mixture was concentrated in vacuo and purified by chromatography on silica gel with heptane:EtOAc (9:1, v/v) as eluent to afford the title compound (440 mg, 48%) as a pale yellow solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by chromatography on silica gel with heptane:EtOAc (9:1

Sources & evidence

ORD record
ord-2b8967049633402ba141b7d6025c334e
Source dataset
uspto-grants-2011_01
Patent number
US07868017B2

Linked notes

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