Bromoform → 5-Bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole

HRID 2103415Notes

Reaction equation

HRID 2103415 reaction equation
C(ON=O)(C)(C)C.N[C:9]1[N:13]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:12]=[C:11]([C:26]#[N:27])[C:10]=1[S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29].C(Br)(Br)[Br:36]>>[Br:36][C:9]1[N:13]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:12]=[C:11]([C:26]#[N:27])[C:10]=1[S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29]

Participants

4

Reactant 3

HCID 5558BromoformHCID 10906Tert-Butyl nitrite2×HCID 3078139Fipronil sulfone

Product 1

HCID 167270545-Bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazoleYield 79%

Conditions

Temperature
65 °C

Procedure

t-Butylnitrite (84 ml, 0.662 mol) was added to a suspension of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole (100 g, 0.221 mol) in bromoform (320 ml). The resulting mixture was heated to 60-70° C. for 3 hours. Another portion of t-butylnitrite (84 ml, 0.662 mol) was added and the mixture stirred at 60-70° C. for a further 2.5 hours. It was then cooled, washed with hexane, hexane-toluene, and then filtered. The solid was washed with pentane and vacuum dried to give 5-bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole as a yellow solid (96.69 g, 79% yield), mp 142° C.

Workup

  1. temperatureIt was then cooled
  2. washwashed with hexane, hexane-toluene
  3. filtrationfiltered
  4. washThe solid was washed with pentane and vacuum
  5. customdried

Sources & evidence

ORD record
ord-85e312b58d134391a55c45452b992ceb
Source dataset
uspto-grants-2009_08
Patent number
US07576107B2

Reaction notes

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