Acetic Acid → Methyl 2-chloro-3-nitrobenzoate

HRID 1368404Notes

Reaction equation

HRID 1368404 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-0e771c33fbeb4c0f98f16f7fa06c0bfd
Source dataset
uspto-grants-2003_06
Patent number
US06573293B2

Reaction notes

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