Bromoform → HCID 13748058, compound

HRID 1381570Notes

Reaction equation

HRID 1381570 reaction equation
N[C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[CH:4][C:3]=1[S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20].N(OC(C)(C)C)=O.ClCCl.C(Br)(Br)[Br:37]>>[Br:37][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[CH:4][C:3]=1[S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20]

Participants

5

Reactant 4

HCID 5558Bromoform2×HCID 6344DichloromethaneHCID 10906Tert-Butyl nitriteHCID 13786177HCID 13786177, compound

Product 1

HCID 13748058HCID 13748058, compoundYield 43%

Procedure

A suspension of 28 g (0.065 mole) of 5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-trifluoromethylsulphonyl-pyrazole in 70 ml of bromoform are added to a solution of 15.5 ml (0.13 mole) of t-butyl nitrite in 30 ml of bromoform at 20° C. to 25° C. The temperature rises to 40° C. The mixture is then stirred for 15 hours at room temperature, 200 ml of dichloromethane are added, the mixture is washed in sequence with aqueous sodium hydrogen carbonate, sodium thiosulphate and sodium chloride solution, the organic phase is dried over magnesium sulphate and the solvent is removed in vacuo. The oil remaining is purified by chromatography (silica gel, eluent: dichloromethane). 13.8 g (43% of theory) of 5-bromo-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-trifluoromethylsulphonylpyrazole of melting point 90° C. to 91° C. are obtained.

Workup

  1. customrises to 40° C
  2. washthe mixture is washed in sequence with aqueous sodium hydrogen carbonate, sodium thiosulphate and sodium chloride solution
  3. dry with materialthe organic phase is dried over magnesium sulphate
  4. customthe solvent is removed in vacuo
  5. customThe oil remaining is purified by chromatography (silica gel, eluent: dichloromethane)

Sources & evidence

ORD record
ord-aa5b1664094c47feb50ec679911da8e4
Source dataset
uspto-grants-1989_02
Patent number
US04803215

Reaction notes

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