Hydrogen Peroxide → HCID 24785465, compound

HRID 523455Notes

Reaction equation

HRID 523455 reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].Br[CH2:16][C:17]1[N:21]([C:22]2[C:27]([Cl:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[CH:24][C:23]=2[Cl:33])[N:20]=[C:19]([C:34]#[N:35])[C:18]=1[S:36][C:37]([F:40])([F:39])[F:38].OO.O>C1COCC1.C(OCC)(=O)C>[C:34]([C:19]1[C:18]([S:36][C:37]([F:38])([F:40])[F:39])=[C:17]([CH3:16])[N:21]([C:22]2[C:27]([Cl:28])=[CH:26][C:25]([C:29]([F:31])([F:32])[F:30])=[CH:24][C:23]=2[Cl:33])[N:20]=1)#[N:35]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 3611392Lithium tri-s-butylborohydrideHCID 25179438HCID 25179438, compound

Product 1

HCID 24785465HCID 24785465, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of L-selectride (14.2 mL, 1M in THF) was added to a solution of 5-bromomethyl-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole (6.75 g) in THF at −78° C. The reaction mixture was allowed to warm to room temperature with stirring over one hour, and then hydrogen peroxide (2.6 mL, 30% w/v) was added followed by water and ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography (SiO2, heptane/EA) to afford the title compound as a white solid (3.67 g, 65%). MS (ES): M/Z [M+NH4]=437. 1H NMR: (400 MHz, DMSO-d6): 2.30 (s, 3H) and 8.39 (s, 2H). 19F NMR (376 MHz, DMSO-d6): −44.03 (s, 3F) and −61.98 (s, 3F).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by chromatography (SiO2, heptane/EA)

Sources & evidence

ORD record
ord-fffc551938dd4a538277ff2d0b860210
Source dataset
uspto-grants-2016_05
Patent number
US09339033B2

Reaction notes

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