Water → HCID 9806996, compound
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[C:25]([C:27]1[C:31]([CH:32]2[CH2:35][C:34](=O)[CH2:33]2)=[CH:30][N:29]([C:37]2[C:42]([Cl:43])=[CH:41][C:40]([C:44]([F:47])([F:46])[F:45])=[CH:39][C:38]=2[Cl:48])[N:28]=1)#[N:26].O>C(Cl)Cl>[C:25]([C:27]1[C:31]([CH:32]2[CH2:35][C:34](=[C:20]([Br:24])[Br:21])[CH2:33]2)=[CH:30][N:29]([C:37]2[C:38]([Cl:48])=[CH:39][C:40]([C:44]([F:45])([F:46])[F:47])=[CH:41][C:42]=2[Cl:43])[N:28]=1)#[N:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
Triphenylphosphine (560 mg, 2.14 mmol) was dissolved in 2 ml anhydrous DCM and cooled to -10° C. Carbon tetrabromide (355 mg, 1.07 mmol in 2 ml DCM) was added dropwise to the cooled solution, producing an amber colour. 3-Cyano-4-(3-oxocyclobutyl)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (200 mg, 0.53 mmol, Example 3) in DCM (2 ml) was added dropwise whereupon the reaction mixture assumed a brown colour. The reaction mixture was warmed to room temperature. After 0.5 hr the mixture was poured into water (20 ml) and extracted with DCM (3×20 ml). The combined organics were washed (brine), dried (Na2SO4), filtered and the solvent removed in vacuo to leave a brown solid. This was purified by silica chromatography (eluting with 50% DCM/hexane) to yield 230 mg of the title compound as a white solid.
Workup
- customproducing an amber colour
- temperatureThe reaction mixture was warmed to room temperature
- extractionextracted with DCM (3×20 ml)
- washThe combined organics were washed (brine)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customthe solvent removed in vacuo
- customto leave a brown solid
- customThis was purified by silica chromatography (eluting with 50% DCM/hexane)
Sources & evidence
- ORD record
- ord-3608dba40bc14af8a64ffaf59327456a
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06077859
Reaction notes
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