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

HRID 742189Notes

Reaction equation

HRID 742189 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 with stirring to 27.5 g (0.133 mole) of methyl 2-methylphenylglyoxylate O-methyloxime, dissolved in 400 ml of tetrachloromethane. The mixture is then refluxed for four hours while being exposed 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
  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-e7a95cc3139a4803be0f7f3f0c729cb4
Source dataset
uspto-grants-1996_09
Patent number
US05554578

Reaction notes

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