Acetic Acid → Methyl 2-chloro-3-nitrobenzoate

HRID 2101544Notes

Reaction equation

HRID 2101544 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-carboxynitrobenzene 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-6e48c4032b0841b6a2b7d58a3a5ef5e3
Source dataset
uspto-grants-2009_08
Patent number
US07572924B2

Reaction notes

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