Hydrochloric Acid → HCID 22918648, compound

HRID 1376908Notes

Reaction equation

HRID 1376908 reaction equation
[Br:1][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6]C)=[O:4].[Br:17]Br.C[O-].[Na+].Cl>CO>[Br:1][C:2]([Br:17])([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 10424182Ethyl alpha-bromo-4-nitrobenzeneacetateHCID 10942334Sodium Methoxide

Product 1

HCID 22918648HCID 22918648, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

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%).

Workup

  1. extractionextracted with dichloromethane
  2. customThe dichloromethane solution was evaporated

Sources & evidence

ORD record
ord-a80e2a1a7b7d4eff88f76c822893beac
Source dataset
uspto-grants-1997_09
Patent number
US05663371

Reaction notes

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