Acetic Acid → Methyl 2-chloro-3-nitrobenzoate

HRID 1008143Notes

Reaction equation

HRID 1008143 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Cl:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19].C(O)(=O)C>CCCCCC.CO>[Cl:8][C:9]1[C:14]([C:15]([O:17][CH3:1])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 198702-Chloro-3-nitrobenzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 10751184Methyl 2-chloro-3-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

A solution of trimethylsilyldiazomethane in hexane (2 M) was added dropwise to a solution of 2.01 g 2-chloro-3-carboxy-nitrobenzene in 20 mL methanol at room temperature until no further gas evolution occurred. Acetic acid was then added to quench excess trimethylsilyldiazomethane. The reaction mixture was evaporated under vacuum and the residue was dried in an oven overnight. The 2-chloro-3-methoxycarbonylnitrobenzene obtained was pure enough for the following reaction.

Workup

  1. customto quench excess trimethylsilyldiazomethane
  2. customThe reaction mixture was evaporated under vacuum
  3. customthe residue was dried in an oven overnight

Sources & evidence

ORD record
ord-ecafd3ea790e46169f9a5f5429f06f49
Source dataset
uspto-grants-2004_09
Patent number
US06797725B2

Reaction notes

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