Trimethylsilyldiazomethane → Methyl 4-amino-3-bromo-5-nitrobenzoate

HRID 592318Notes

Reaction equation

HRID 592318 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])=[CH:4][C:3]=1[Br:14].[CH3:15][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([O:8][CH3:15])=[O:7])=[CH:4][C:3]=1[Br:14]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 547587704-Amino-3-bromo-5-nitrobenzoic acid

Product 1

HCID 13685347Methyl 4-amino-3-bromo-5-nitrobenzoateYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-3-bromo-5-nitrobenzoic acid (3.65 g, 14.0 mmol) in dichloromethane (35 mL) and methanol (35 mL) at 0° C. was slowly added trimethylsilyl-diazomethane (8.74 mL, 17.5 mmol). The mixture was allowed to warm to ambient temperature and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) gave the title compound (1.54 g). LC-MS [M]=275.1.

Workup

  1. customat 0° C.
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-4f3a9c84fc614cf98f51713fec7f35d5
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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