Water → 4-(2-Bromofuran-3-yl)-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

HRID 1108834Notes

Reaction equation

HRID 1108834 reaction equation
[C:1]([C:3]1[C:7]([C:8]2[CH:12]=[CH:11][O:10][CH:9]=2)=[CH:6][N:5]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[Cl:24])[N:4]=1)#[N:2].[Br:25]N1C(=O)CCC1=O.CCOCC.O>O1CCCC1>[Br:25][C:9]1[O:10][CH:11]=[CH:12][C:8]=1[C:7]1[C:3]([C:1]#[N:2])=[N:4][N:5]([C:13]2[C:14]([Cl:24])=[CH:15][C:16]([C:20]([F:23])([F:21])[F:22])=[CH:17][C:18]=2[Cl:19])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 221208903-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(furan-3-yl)pyrazole

Product 1

HCID 98038424-(2-Bromofuran-3-yl)-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(furan-3-yl)pyrazole (0.19 g) in tetrahydrofuran (5 ml) was added portionwise N-bromosuccinimide (0.093 g). The mixture was left at room temperature for 24 hours and then poured into ether (15 ml) and water (15 ml). The layers were separated and the organic layer was dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (10 g) eluted with hexane:dichloromethane (1:1). Combination and evaporation of suitable fractions gave the title compound as a white solid, m.p. 111° C.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel (10 g)
  5. washeluted with hexane:dichloromethane (1:1)
  6. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-cdf78d2927db4fceb0c4871a5028590d
Source dataset
uspto-grants-2000_05
Patent number
US06069157

Reaction notes

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