Hydrochloric Acid → HCID 54252801, compound

HRID 1584715Notes

Reaction equation

HRID 1584715 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4](=[N:12][OH:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][F:23].Cl>CS(C)=O.O>[F:23][CH2:22][O:13][N:12]=[C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])[C:3]([O:2][CH3:1])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 61108BromofluoromethaneHCID 73656259HCID 73656259, compound

Product 1

HCID 54252801HCID 54252801, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 57 g of 2-tolylglyoxylic acid methyl ester oxime and 80 g of powdered potassium carbonate is mixed into 550 ml of dimethyl sulfoxide for 30 minutes at room temperature and then a solution of 40 g of bromofluoromethane in 30 ml of dimethyl sulfoxide is added dropwise at room temperature. The reaction mixture is stirred for a further 20 hours and then poured into 1200 ml of water, neutralised with 230 ml of hydrochloric acid and extracted four times with 250 ml of ethyl acetate each time. The combined organic phases are washed with 200 ml of saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation in vacuo. Purification by flash chromatography (silica gel, ethyl acetate/hexane 1:9) yields 2-tolylglyoxylic acid methyl ester O-fluoromethyloxime in the form of a viscous oil.

Workup

  1. extractionextracted four times with 250 ml of ethyl acetate each time
  2. washThe combined organic phases are washed with 200 ml of saturated sodium chloride solution
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated by evaporation in vacuo
  5. customPurification by flash chromatography (silica gel, ethyl acetate/hexane 1:9)

Sources & evidence

ORD record
ord-d2f32dbfd58843debc2d24e2f31523ea
Source dataset
uspto-grants-1999_08
Patent number
US05935908

Reaction notes

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