Bromine → HCID 10734647, compound

HRID 1376906Notes

Reaction equation

HRID 1376906 reaction equation
[Cl:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:16])[CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[Br:17]Br.C[O-].[Na+]>CO>[Br:17][C:2]([Cl:1])([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:16])[CH:8]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 24408BromineHCID 10942334Sodium MethoxideHCID 10999245HCID 10999245, compound

Product 1

HCID 10734647HCID 10734647, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-chloro-2-(3-methyl-4-nitrophenyl)acetate (6 g) in methanol (20 cm3) was stirred at room temperature and the solutions of bromine and sodium methoxide were added dropwise and simultaneously. The methanol was removed from the reaction mixture under vacuum and the residue was dissolved in dichloromethane. The dichloromethane solution was washed with water, separated and evaporated to have a residue which was recrystallised from ethanol to give yellow methyl 2-bromo-2-chloro-2-(3-methyl-4-nitrophenyl)acetate (4.0 g, 50%).

Workup

  1. customThe methanol was removed from the reaction mixture under vacuum
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe dichloromethane solution was washed with water
  4. customseparated
  5. customevaporated
  6. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-7214885a839344078d65574b4448c89e
Source dataset
uspto-grants-1997_09
Patent number
US05663371

Reaction notes

Loading…