Hydrochloric Acid → HCID 86761700, compound

HRID 1880247Notes

Reaction equation

HRID 1880247 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([C:24]([F:27])([F:26])[F:25])=[CH:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([Cl:23])[CH:17]=2)=O)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[OH-:28].[Na+].S(O)(O)(=O)=O.[NH2:35]O.Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([C:12]2([C:24]([F:27])([F:26])[F:25])[O:28][N:35]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([Cl:23])[CH:17]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)HCID 86761698HCID 86761698, compound

Product 1

HCID 86761700HCID 86761700, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

Into a solution of 4.02 g of 3-[3-bromo-5-(trifluoromethyl)phenyl]-1-(3-chloro-4-methylphenyl)-4,4,4-trifluoro-2-butene-1-one and 0.82 g of tetrabutylammonium bromide in 23 mL of toluene, a solution of 1.03 g of sodium hydroxide in 2.4 mL of water and a solution of 0.98 g of hydroxylamine sulfate in 3.9 mL of water were dropped while ice-cooling and stirring the solution and after the completion of the dropping, the resultant mixture was stirred at room temperature for 15 hours. After the completion of the reaction, 7.11 g of concentrated hydrochloric acid was added to the reaction mixture while ice-cooling and stirring the reaction mixture. The organic phase was separated off and then was washed with 10 mL of a 3N hydrochloric acid aqueous solution, 10 mL of water and 10 mL of a saturated sodium hydrogen carbonate aqueous solution in this order. Subsequently, the organic phase was dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by alumina column chromatography eluting with chloroform to obtain 3.56 g of the objective substance as a yellow resinoid.

Workup

  1. temperaturecooling
  2. additionwas added to the reaction mixture while ice-
  3. temperaturecooling
  4. stirringstirring the reaction mixture
  5. customThe organic phase was separated off
  6. washwas washed with 10 mL of a 3N hydrochloric acid aqueous solution, 10 mL of water and 10 mL of a saturated sodium hydrogen carbonate aqueous solution in this order
  7. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resultant residue was purified by alumina column chromatography
  10. washeluting with chloroform
  11. customto obtain 3.56 g of the objective substance as a yellow resinoid

Sources & evidence

ORD record
ord-ed3b4c627680450787d13c33fcae85f6
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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