Thionyl Chloride → 2-Chloro-3-nitro-5-trifluoromethylbenzoyl chloride

HRID 550347Notes

Reaction equation

HRID 550347 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:3]=1[C:4](O)=[O:5].O=S(Cl)[Cl:20]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:3]=1[C:4]([Cl:20])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 100844572-chloro-3-nitro-5-(trifluoromethyl)benzoic Acid

Product 1

HCID 200341672-Chloro-3-nitro-5-trifluoromethylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-chloro-3-nitro-5-trifluoromethylbenzoic acid (1.35 g) in toluene (15 ml) are added 1.2 ml of SOCl2. After refluxing for 2 hours, the end of the reaction is confirmed by monitoring by infrared (new band at 1788 cm−1). The reaction medium is evaporated to dryness and the resulting yellow oil, 2-chloro-3-nitro-5-trifluoromethylbenzoyl chloride, is used without further purification in the following step.

Workup

  1. temperatureAfter refluxing for 2 hours
  2. customThe reaction medium is evaporated to dryness
  3. customthe resulting yellow oil, 2-chloro-3-nitro-5-trifluoromethylbenzoyl chloride, is used without further purification in the following step

Sources & evidence

ORD record
ord-ff50158b04b64ee09384d10d96283c6c
Source dataset
uspto-grants-2011_05
Patent number
US07947675B2

Reaction notes

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