2-Methyl-3-nitrobenzoic acid → 2-Methyl-3-nitrobenzoyl chloride

HRID 262068Notes

Reaction equation

HRID 262068 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].P(Cl)(Cl)(Cl)(Cl)[Cl:15].P(Br)(Br)(Br)(Br)Br.S(Cl)(Cl)=O>C1C=CC=CC=1>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

6

Reactant 4

HCID 160962-Methyl-3-nitrobenzoic acid2×HCID 24386Thionyl Chloride2×HCID 24819Phosphorus pentachlorideHCID 62678Phosphorus pentabromide

Product 1

HCID 121948722-Methyl-3-nitrobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The conversion of 2-methyl-3-nitrobenzoic acid (II) to a 2-methyl-3-nitrobenzoyl halide (III) may be effected by reacting II with a suitable halogenating agent, such as phosphorus pentachloride, phosphorus pentabromide, thionyl chloride, and the like, preferably thionyl chloride, in a suitable inert solvent, such as dry benzene, at a temperature from room temperature to reflux until the reaction is complete and removing the solvent under reduced pressure. Preferably, II is converted to 2-methyl-3-nitrobenzoyl chloride by simply refluxing it in pure thionyl chloride for about 2- 6 hours and removing the excess thionyl chloride under reduced pressure. The preferred 2-methyl-3-nitrobenzoyl chloride is obtained in yields of 95- 100% of theoretical.

Workup

  1. customremoving the solvent under reduced pressure
  2. temperatureby simply refluxing it in pure thionyl chloride for about 2- 6 hours
  3. customremoving the excess thionyl chloride under reduced pressure

Sources & evidence

ORD record
ord-93d9c116db2c4d8cba73677ccbc2f215
Source dataset
uspto-grants-1979_05
Patent number
US04153632

Reaction notes

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