Bromine → Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate

HRID 1534566Notes

Reaction equation

HRID 1534566 reaction equation
[Br:1]Br.[CH3:3][O:4][N:5]=[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:7]([O:9][CH3:10])=[O:8]>ClC(Cl)(Cl)Cl>[CH3:3][O:4][N:5]=[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][Br:1])[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 24408BromineHCID 54500888Methyl 2-(methoxyimino)-2-(2-methylphenyl)acetate

Product 1

HCID 54028047Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetateYield 46%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

21.4 g (0.133 mole) of bromine are added to 27.5 g (0.133 mole) of methyl 2-methylphenylglyoxylate O-methyloxime, dissolved in 400 ml of tetrachloromethane, while stirring. The mixture is then refluxed for four hours with exposure to a 300 W Hg vapor lamp. It is then evaporated down, the residue is taken up in ethyl acetate/water and the solution is washed with H2O, dried with sodium sulfate and evaporated down. The crude product is purified by chromatography over silica gel using 9:1 cyclohexane/ethyl acetate. 17.4 g (46%) of the abovementioned compound are obtained as an oil.

Workup

  1. temperatureThe mixture is then refluxed for four hours with exposure to a 300 W Hg vapor lamp
  2. customIt is then evaporated down
  3. washthe solution is washed with H2O
  4. dry with materialdried with sodium sulfate
  5. customevaporated down
  6. customThe crude product is purified by chromatography over silica gel using 9:1 cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-e75fd180fbc440dbb34a7981db56d761
Source dataset
uspto-grants-1992_02
Patent number
US05089528

Reaction notes

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