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

HRID 729042Notes

Reaction equation

HRID 729042 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.C(OCC)(=O)C.O>[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

5

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 2

HCID 5943Carbon TetrachlorideSolventHCID 22728543Water ethylacetateSolvent

Procedure

21.4 g (0.133 mole) of bromine are added to 27.5 g (0.133 mole) of 2-methylphenylglyoxylic acid methyl ester O-methyloxime dissolved in 400 ml of tetrachloromethane, while stirring. Thereafter, the mixture is refluxed for four hours with exposure to a 300 W Hg vapor lamp. It is thenevaporated 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 is obtained as an oil.

Workup

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

Sources & evidence

ORD record
ord-d6ad2439beeb42e086a1231dd2af95e4
Source dataset
uspto-grants-1991_09
Patent number
US05051447

Reaction notes

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