Thionyl Chloride → 2,6-Difluoro-3-nitrobenzoyl chloride

HRID 1187295Notes

Reaction equation

HRID 1187295 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([F:14])[C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:17])=O>CN(C)C=O>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([F:14])[C:3]=1[C:4]([Cl:17])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3026292,6-Difluoro-3-nitrobenzoic acid

Product 1

HCID 27817562,6-Difluoro-3-nitrobenzoyl chlorideYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
80 °C

Procedure

To 2,6-difluoro-3-nitro-benzoic acid (48, 5.50 g, 27.1 mmol), thionyl chloride (20 mL, 300 mmol) is added, followed by N,N-dimethylformamide (0.1 mL, 2.0 mmol) and the reaction is heated in an oil bath at 80° C. After overnight reaction, the reaction mixture is concentrated under vacuum, azeotroped with toluene (2×) to provide the desired compound (49, 5.95 g).

Workup

  1. customAfter overnight reaction
  2. concentrationthe reaction mixture is concentrated under vacuum
  3. customazeotroped with toluene (2×)

Sources & evidence

ORD record
ord-e273014afdf8454e803f449bad05b05d
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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