Hexane → Methyl 3-acetylamino-6-bromo-2-nitrobenzoate

HRID 1835105Notes

Reaction equation

HRID 1835105 reaction equation
[C:1]([NH:4][C:5]1[C:6]([N+:15]([O-:17])=[O:16])=[C:7]([C:11]([Br:14])=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2].[CH3:18][Si](C=[N+]=[N-])(C)C.CCCCCC>C1COCC1.CO>[CH3:18][O:9][C:8](=[O:10])[C:7]1[C:11]([Br:14])=[CH:12][CH:13]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[C:6]=1[N+:15]([O-:17])=[O:16]

Participants

6

Reactant 3

HCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 114039033-Acetylamino-6-bromo-2-nitro-benzoic acid

Product 1

HCID 11151255Methyl 3-acetylamino-6-bromo-2-nitrobenzoateYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-acetylamino-6-bromo-2-nitro-benzoic acid (3.86 g, 14.96 mmol) in dry THF (42 mL) and dry methanol (18 mL) was added a solution of (trimethylsilyl)diazomethane in hexane (2M, 24 mL, 48 mmol). The solution was stirred at room temperature for 3 h and evaporated. The residue was purified by flash chromatography in hexanes/ethyl acetate (6:1) to give 3-acetylamino-6-bromo-2-nitrobenzoic acid methyl ester (2.45 g, 52%).

Workup

  1. customevaporated
  2. customThe residue was purified by flash chromatography in hexanes/ethyl acetate (6:1)

Sources & evidence

ORD record
ord-1ae964ac975345e4b56f72cdac56d34d
Source dataset
uspto-grants-2004_08
Patent number
US06770639B2

Reaction notes

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