Bromomethylcyclopropane → HCID 54307501, compound

HRID 1457092Notes

Reaction equation

HRID 1457092 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[C:4]([Cl:17])=[C:5]([C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=1)[C:6](=[N:8][OH:9])[NH2:7].[CH:20]1([CH2:23]Br)[CH2:22][CH2:21]1>C(Cl)(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:20]1([CH2:23][O:9][N:8]=[C:6]([NH2:7])[C:5]2[C:10]([C:13]([F:15])([F:14])[F:16])=[CH:11][CH:12]=[C:3]([C:2]([F:18])([F:1])[F:19])[C:4]=2[Cl:17])[CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 81503BromomethylcyclopropaneHCID 54279990HCID 54279990, compound

Product 1

HCID 54307501HCID 54307501, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6212ChloroformSolvent

Procedure

In 10 ml of chloroform was dissolved 0.60 g of 3,6-bistrifluoromethyl-2-chlorobenzamidoxime and 0.50 g of cyclopropylmethylbromide, and to the solution was added 0.1 g of tetrabutylammonium bromide at room temperature with stirring, and then 1.2 ml of 10% aqueous solution of sodiunhydroxide, then stirred for 3 hours at 30°-40° C. The solution was washed with water, washed with saturated saline solution and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography to obtain 0.40 g of the objective compound.m.p. 75°-80° C.

Workup

  1. washThe solution was washed with water
  2. washwashed with saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-393229ebc425459d9cf19d247210adad
Source dataset
uspto-grants-1998_12
Patent number
US05847005

Reaction notes

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