Trimethylsilyldiazomethane → Methyl 2-amino-4-bromo-3-methylbenzoate

HRID 507087Notes

Reaction equation

HRID 507087 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[NH2:8][C:9]1[C:17]([CH3:18])=[C:16]([Br:19])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]>C(OCC)(=O)C.C(O)C>[NH2:8][C:9]1[C:17]([CH3:18])=[C:16]([Br:19])[CH:15]=[CH:14][C:10]=1[C:11]([O:13][CH3:1])=[O:12]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 148855482-Amino-4-bromo-3-methylbenzoic acid

Product 1

HCID 22890262Methyl 2-amino-4-bromo-3-methylbenzoateYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add (trimethylsilyl)diazomethane (16.5 mL, 33 mmol, 2 M in hexane) to a solution of 2-amino-4-bromo-3-methyl-benzoic acid (3.8 g, 16.5 mmol) in ethyl acetate (50 mL) and ethanol (50 mL) at room temperature and stir the solution for 16 h. Remove the solvent under reduced pressure. Chromatograph the residue over silica gel, eluting with hexanes/ethyl acetate, to afford the title compound (3.54 g, 88%). MS (ES+): 245 (M+H).

Workup

  1. customRemove the solvent under reduced pressure
  2. washChromatograph the residue over silica gel, eluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-6ab3e58b2d5844cf904791881b1e8bb0
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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