Bromoform → HCID 10275860, compound

HRID 861244Notes

Reaction equation

HRID 861244 reaction equation
[NH2:1][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]=[C:4]([C:19]([F:22])([F:21])[F:20])[C:3]=1C#N.[CH:25]([Br:28])(Br)Br.N(OC(C)(C)C)=O>>[Br:28][C:25]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:16])([F:17])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]([F:20])([F:22])[F:21])[C:3]=1[C:2]#[N:1]

Participants

4

Reactant 3

HCID 5558BromoformHCID 10906Tert-Butyl nitriteHCID 101349005-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 10275860HCID 10275860, compound

Conditions

Temperature
50 °C

Procedure

A stirred mixture of 5-amino-4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethylpyrazole (3.89 g) and bromoform (13 ml) was treated with tert-butyl nitrite (2.26 ml) at room temperature. After 15 minutes the mixture was heated to 50° C. for 1 hour, and evaporated in vacuo to yield a red oil. This was purified by chromatography on silica (Merck, 40°-230 mesh, 0.7 kg cm-2) eluting with a mixture of dichloromethane and petroleum ether (1:2) to furnish 5-bromo-4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethylpyrazole as a fawn solid m.p. 85°-87° C. (3.7 g).

Workup

  1. customevaporated in vacuo
  2. customto yield a red oil
  3. customThis was purified by chromatography on silica (Merck, 40°-230 mesh, 0.7 kg cm-2)
  4. washeluting with a mixture of dichloromethane and petroleum ether (1:2)

Sources & evidence

ORD record
ord-d322813509fe4af9bbd5b0cbc32fa1f2
Source dataset
uspto-grants-1998_02
Patent number
US05714191

Reaction notes

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