Thionyl Chloride → 2-Fluoro-4-nitrobenzoyl chloride

HRID 1874073Notes

Reaction equation

HRID 1874073 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:16])=O>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3026792-Fluoro-4-nitrobenzoic acid

Product 1

HCID 104204352-Fluoro-4-nitrobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-fluoro-4-nitrobenzoic acid (5.0 g, 27.0 mmol) in 70 mL DCM is added thionyl chloride (12.1 mL, 162 mmol). The reaction mixture is stirred at 50° C. for 1.5 h and overnight at RT. The reaction mixture is concentrated in vacuo, the residue is taken up in fresh DCM and concentrated in vacuo again. Yield: 5.12 g.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. concentrationconcentrated in vacuo again

Sources & evidence

ORD record
ord-e49cf6abe38042e09d8cb3a05fa457b2
Source dataset
uspto-grants-2012_11
Patent number
US08304556B2

Reaction notes

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