Triphenylphosphine → HCID 86749136, compound

HRID 2259507Notes

Reaction equation

HRID 2259507 reaction equation
[Cl:1][C:2]1[O:10][C:9]2[C:4](=[N:5][C:6]([CH3:11])=[CH:7][CH:8]=2)[C:3]=1[Cl:12].[Br:13]N1C(=O)CCC1=O.[C:21]1([P:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)(Cl)(Cl)Cl.CC#N.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br-:13].[Cl:1][C:2]1[O:10][C:9]2[C:4](=[N:5][C:6]([CH2:11][P+:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:7][CH:8]=2)[C:3]=1[Cl:12]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 19002930HCID 19002930, compound

Product 1

HCID 86749136HCID 86749136, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,3-dichloro-5-methylfurano[3,2-b]pyridine (0.5 g, 2.47 mmol) in CCl4 (15 mL) was added N-bromosuccinimide (0.44 g, 2.47 mmol) and benzoyl peroxide (2 mg). The mixture was stirred and photolyzed using a sun lamp for 1 hr. The resulting mixture was cooled and filtered through celite. Evaporation of the filtrate gave an oil which was then dissolved in CH3CN (10 mL). Triphenylphosphine (1.29 g, 4.94 mmol) was added and the mixture was stirred at r.t. for 20 hr. The solvent was removed and the residue was triturated with ether to afford 1 g (77%) of the title compound after filtration.

Workup

  1. customfor 1 hr
  2. temperatureThe resulting mixture was cooled
  3. filtrationfiltered through celite
  4. customEvaporation of the filtrate
  5. customgave an oil which
  6. stirringthe mixture was stirred at r.t. for 20 hr
  7. customThe solvent was removed
  8. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-a8679e05131d41c39a628cf2d431498d
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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