Carbon tetrabromide → HCID 86619475, compound

HRID 254811Notes

Reaction equation

HRID 254811 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]([C:29]1[O:33][C:32]([C:34]2[C:38]([CH:39]=O)=[C:37]([C:41]3[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=3)[N:36]([C:48]3[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][C:49]=3[Cl:55])[N:35]=2)=[N:31][N:30]=1)([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[C:25]([C:29]1[O:33][C:32]([C:34]2[C:38]([CH:39]=[C:1]([Br:5])[Br:2])=[C:37]([C:41]3[CH:42]=[CH:43][C:44]([Cl:47])=[CH:45][CH:46]=3)[N:36]([C:48]3[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][C:49]=3[Cl:55])[N:35]=2)=[N:31][N:30]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 25150438HCID 25150438, compound

Product 1

HCID 86619475HCID 86619475, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of carbontetrabromide (313 mg, 0.94 mmol) in methylene chloride (15 ml) at 0° C. was added triphenylphosphine (248 mg, 0.95 mmol). The reaction mixture was stirred at 0° C. for 10 minutes and then 3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbaldehyde (300 mg, 0.63 mmol) in methylenechloride (10 ml) was added slowly. The reaction temperature was warmed slowly to room temperature and stirred overnight. The resulting solution was quenched with saturated ammonium chloride and extracted organic layer with ethyl ether (50 ml twice). After evaporation, crude residue was purified with silica gel column (hexane/ethyl acetate=5/1) to recover starting material (110 mg, 37%) and produce 2-tert-butyl-5-(5-(4-chlorophenyl)-4-(2,2-dibromovinyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl)-1,3,4-oxadiazole (230 mg, 58% yield) as white solid.

Workup

  1. temperatureThe reaction temperature was warmed slowly to room temperature
  2. stirringstirred overnight
  3. customThe resulting solution was quenched with saturated ammonium chloride
  4. extractionextracted organic layer with ethyl ether (50 ml twice)
  5. customAfter evaporation, crude residue
  6. customwas purified with silica gel column (hexane/ethyl acetate=5/1)
  7. customto recover

Sources & evidence

ORD record
ord-4f638c8665d1471bb90b3e962a54047a
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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