Trimethylsilyldiazomethane → 5-Fluoro-2-nitrobenzoic acid methyl ester

HRID 1593076Notes

Reaction equation

HRID 1593076 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:14][Si](C=[N+]=[N-])(C)C>C1COCC1.C(OCC)(=O)C>[CH3:14][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 51520495-Fluoro-2-nitrobenzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-fluoro-2-nitro-benzoic acid (1 g, 5.4 mmol in 5 mL THF, was added (trimethylsilyl)diazomethane (2 M in ether, 11 ml, 22 mmol) at 0° C. The reaction mixture was warmed to room temperature under argon and stirred for 30 minutes, then diluted with ethyl acetate and washed with brine. The organic layers were combined and concentrated in vacuo to give a crude residue, which was purified by column chromatography (silica 5-30% EtOAc/hexane) to give 5-fluoro-2-nitro-benzoic acid methyl ester.

Workup

  1. washwashed with brine
  2. concentrationconcentrated in vacuo
  3. customto give a crude residue, which
  4. customwas purified by column chromatography (silica 5-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-d64bb13b5d624b8592725d54d0e3c8da
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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