Bromine → HCID 18401356, compound

HRID 1018420Notes

Reaction equation

HRID 1018420 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[C:13]([S:15][CH3:16])[N:12]([CH3:17])[N:11]=2)=[C:6]([F:18])[CH:5]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:14]1[C:10]([C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][C:6]=2[F:18])=[N:11][N:12]([CH3:17])[C:13]=1[S:15][CH3:16]

Participants

4

Reactant 2

HCID 24408BromineHCID 15672355HCID 15672355, compound

Product 1

HCID 18401356HCID 18401356, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

13.7 g (86 mmol) of bromine were added dropwise to a solution of 20 g (78 mmol) of 3-(4-chloro-2-fluorophenyl)-1-methyl-5-methylthio-1H-pyrazole in 400 ml of carbon tetrachloride, and the mixture was then stirred for 3 days. The reaction solution was subsequently washed with saturated aqueous sodium bicarbonate solution and water, dried over magnesium sulfate and finally concentrated. The crude product was purified by silica gel chromatography (mobile phase: hexane/ethyl acetate =9:1). Yield: 22.4 g. 1H-NMR (270 MHz, in CDCl3): δ[ppm]=2.40 (s, 3H), 4.06 (s, 3H), 7.15-7.25 (m, 2H), 7.48 (t, 1H).

Workup

  1. washThe reaction solution was subsequently washed with saturated aqueous sodium bicarbonate solution and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationfinally concentrated
  4. customThe crude product was purified by silica gel chromatography (mobile phase: hexane/ethyl acetate =9:1)

Sources & evidence

ORD record
ord-1195715a3b3f4157b5fb27aa4d9882f3
Source dataset
uspto-grants-2002_11
Patent number
US06482774B1

Reaction notes

Loading…