Carbon tetrabromide → HCID 21188128, compound

HRID 1383596Notes

Reaction equation

HRID 1383596 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[Cl:25][C:26]1[N:30]([C:31]2[C:36]([Cl:37])=[CH:35][C:34]([C:38]([F:41])([F:40])[F:39])=[CH:33][C:32]=2[Cl:42])[N:29]=[C:28]([C:43]#[N:44])[C:27]=1[CH:45]=O>ClCCl>[Cl:25][C:26]1[N:30]([C:31]2[C:32]([Cl:42])=[CH:33][C:34]([C:38]([F:40])([F:39])[F:41])=[CH:35][C:36]=2[Cl:37])[N:29]=[C:28]([C:43]#[N:44])[C:27]=1[CH:45]=[C:20]([Br:24])[Br:21]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21188083HCID 21188083, compound

Product 1

HCID 21188128HCID 21188128, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of triphenylphosphine (0.709 g) in dry dichloromethane (2 ml) at 0° C. under an atmosphere of dry nitrogen was added carbon tetrabromide (0.358 g) in dry dichloromethane (2 ml) followed by 5-chloro-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)4-formylpyrazole (0.2 g) in dry dichloromethane (3 ml). The mixture was allowed to warm to room temperature and stirring continued overnight. The reaction mixture was washed with water. The aqueous layer was twice extracted with dichloromethane. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica get eluted with hexane dichloromethane (1:1). Combination and evaporation of suitable fractions followed by recrystallisation from hexane gave the title compound as a white solid, m.p. 119.1-119.5° C.

Workup

  1. washThe reaction mixture was washed with water
  2. extractionThe aqueous layer was twice extracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica
  7. customget
  8. washeluted with hexane dichloromethane (1:1)
  9. customCombination and evaporation of suitable fractions
  10. customfollowed by recrystallisation from hexane

Sources & evidence

ORD record
ord-d0d9dbb412b442be812ac66a6f406306
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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