Trimethylsilyldiazomethane → 4-Amino-3-chloro-2-fluoro-5-nitro-benzoic acid methyl ester

HRID 1010057Notes

Reaction equation

HRID 1010057 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:14])[C:3]=1[Cl:15].[Si](C=[N+]=[N-])(C)(C)[CH3:17]>C1COCC1.CO>[CH3:17][O:7][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]([NH2:1])=[C:3]([Cl:15])[C:4]=1[F:14]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 211141824-Amino-3-chloro-2-fluoro-5-nitro-benzoic acid

Product 1

HCID 858681944-Amino-3-chloro-2-fluoro-5-nitro-benzoic acid methyl esterYield 39.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-amino-3-chloro-2-fluoro-5-nitro-benzoic acid 3a (3.61 g, 15.4 mmol) in THF (30 mL) and MeOH (10 mL), TMS diazomethane (9.23 mL, 2.0 M solution in hexanes, 18.5 mmol) is added. After completion of reaction, the reaction mixture is concentrated via rotary evaporation with acetic acid in the trap. The recovered oily solid is triturated with diethyl ether to provide 1.51 g of a yellow solid. The filtrate is concentrated and triturated with diethyl ether to give an additional 0.69 g of yellow solid. A total of 2.20 g (57%) of pure desired product is recovered.

Workup

  1. customAfter completion of reaction
  2. concentrationthe reaction mixture is concentrated via rotary evaporation with acetic acid in the trap
  3. customThe recovered oily solid is triturated with diethyl ether

Sources & evidence

ORD record
ord-bce5bb0f15654e848f21ffecd3764f6d
Source dataset
uspto-grants-2011_07
Patent number
US07973170B2

Reaction notes

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