Trimethylsilyldiazomethane → Methyl 2-amino-6-fluorobenzoate

HRID 2353952Notes

Reaction equation

HRID 2353952 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][Si](C=[N+]=[N-])(C)C>C(OC(=O)C)C.C(O)C>[CH3:12][O:5][C:4](=[O:6])[C:3]1[C:7]([F:11])=[CH:8][CH:9]=[CH:10][C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 5211422-Amino-6-fluorobenzoic acid

Product 1

HCID 2818492Methyl 2-amino-6-fluorobenzoateYield 99.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-Amino-6-fluoro-benzoic acid (3.00 g, 19.3 mmol) in ethylacetate (59 mL) and ethanol (59 mL) and add (trimethylsilyl) diazomethane (19.3 mL, 38.68 mmol, 2M in hexane) at room temperature and stir the solution for 1 h 30 min. Remove the solvent under reduced pressure to afford the title compound (3.26 g, quantitative). MS (ES+): 170 (M+H).

Workup

  1. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-1d406add30c44bbf954ae86771f21aef
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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