Nitrobenzene → Ethyl alpha-bromo-4-nitrobenzeneacetate

HRID 1376907Notes

Reaction equation

HRID 1376907 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:10][CH:11](Br)[C:12]([O:14][CH2:15][CH3:16])=[O:13].CC(C)([O-])C.[K+]>CN(C)C=O>[Br:10][CH:11]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 7416NitrobenzeneHCID 69237Ethyl dibromoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 10424182Ethyl alpha-bromo-4-nitrobenzeneacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Nitrobenzene was treated with ethyl dibromoacetate in dimethylformamide containing potassium tertiarybutoxide at -20° C. to give ethyl 2-bromo-2-(4-nitrophenyl)acetate (1.37 parts) which was dissolved in methanol (50 parts). To this methanol solution was added dropwise separately a solution of bromine (1.72 parts) in methanol (40 parts) and a solution of sodium methoxide (0.56 parts) in methanol (40 parts). The reaction mixture was poured into dilute aqueous hydrochloric acid solution and extracted with dichloromethane. The dichloromethane solution was evaporated to give methyl 2,2-dibromo-2-(4-nitrophenyl)acetate (1.44 parts, 50%).

Sources & evidence

ORD record
ord-5e814284ff1d4b4c86025f516da7b82f
Source dataset
uspto-grants-1997_09
Patent number
US05663371

Reaction notes

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