Trimethylsilyldiazomethane → Methyl 3-cyano-5-fluorobenzoate

HRID 1821585Notes

Reaction equation

HRID 1821585 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:6]([OH:8])=[O:7])#[N:2].[CH3:13][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:6]([O:8][CH3:13])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27579633-Cyano-5-fluorobenzoic acid

Product 1

HCID 26597287Methyl 3-cyano-5-fluorobenzoateYield 100.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyano-5-fluorobenzoic acid (1.0 g, 6.1 mmol) in dichloromethane (5 ml) and methanol (0.5 ml), at 0° C., was added dropwise (trimethylsilyl)diazomethane (2M in hexanes, 3.6 ml, 7.3 mmol). The reaction mixture was stirred at room temperature, under nitrogen, for 18 h and then concentrated in vacuo to give the title compound (1.1 g).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ad259722840437abcea4c5a408d9c23
Source dataset
uspto-grants-2009_10
Patent number
US07608604B2

Reaction notes

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