Chlorodifluoromethane → HCID 15239016, compound

HRID 2395934Notes

Reaction equation

HRID 2395934 reaction equation
BrC1C=C(C)C=C2C=1N=C(O)C=N2.[Br:14][C:15]1[CH:16]=[C:17]([CH3:26])[CH:18]=[C:19]2[C:24]=1[N:23]=[CH:22][C:21]([OH:25])=[N:20]2.[OH-].[Na+].[CH:29](Cl)([F:31])[F:30]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1.CCCCCC.C(OCC)C.O>[Br:14][C:15]1[CH:16]=[C:17]([CH3:26])[CH:18]=[C:19]2[C:24]=1[N:23]=[CH:22][C:21]([O:25][CH:29]([F:31])[F:30])=[N:20]2

Participants

10

Reactant 4

HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 178422417HCID 178422417, compoundHCID 178422420HCID 178422420, compound

Product 1

HCID 15239016HCID 15239016, compound

Reagents, catalysts & solvents 5

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 5.0 g (20.9 mmol) of the above isomer mixture of 8-bromo-2-hydroxy-6-methylquinoxaline and 8-bromo-3-hydroxy-6-methylquinoxaline (prepared as in Example 3) and 9.0 g(27.1 mmol) of tetra-n-butylammonium bromide stirring in 150 ml of dioxane,20 g (250.0 mmol) of 50% aqueous sodium hydroxide were added. The reaction mixture was placed under an atmosphere of chlorodifluoromethane (Freon22*)whereby slight pressure was maintained by having a balloon over the reaction flask. A slow exotherm occurred and the mixture stirred 4 h. Excess water and 300 ml of diethyl ether were added. The separated organicextract was washed with water, brine, dried over magnesium sulfate, and evaporated in vacuo to give an oil residue which quickly solidified. Hexane was added, the mixture stirred several minutes, and filtered to give 3.1 g of 8-bromo-3-difluoromethoxy-6-methylquinoxaline. Evaporating the filtrate gave 2.5 g of a crude isomer mixture of 8-bromo-2-difluoromethoxy-6-methylquinoxaline and 8-bromo-3-difluoromethoxy-6-methylquinoxaline.

Workup

  1. additionwere added
  2. temperaturewas maintained
  3. washThe separated organicextract was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customto give an oil residue which
  7. stirringthe mixture stirred several minutes
  8. filtrationfiltered

Sources & evidence

ORD record
ord-803d17577a374db38d8f6ec11f272bbc
Source dataset
uspto-grants-1996_02
Patent number
US05491126

Reaction notes

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