Triphenylphosphine → HCID 57751050, compound

HRID 2283327Notes

Reaction equation

HRID 2283327 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:20]([Cl:24])(Cl)(=[O:22])=[O:21].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:42][C:43]1[N:48]=[CH:47][C:46](/[CH:49]=[CH:50]/S(O)(=O)=O)=[CH:45][CH:44]=1>ClCCl>[Br:42][C:43]1[N:48]=[CH:47][C:46](/[CH:49]=[CH:50]/[S:20]([Cl:24])(=[O:22])=[O:21])=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24648Sulfuryl chlorideHCID 86632008HCID 86632008, compound

Product 1

HCID 57751050HCID 57751050, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triphenylphosphine (2.74 g, 10.44 mmol) was dissolved in anhydrous dichloromethane (30 mL) under an atmosphere of argon and the mixture was cooled to 0° C. with an ice bath. Sulfuryl chloride (0.87 mL, 10.68 mmol) was added dropwise and the cooling bath was removed. The solution was stirred at ambient temperature for 15 min. A solution of (E)-2-(6-bromopyridin-3-yl)ethenesulfonic acid tetrabutylammonium (2.46 g, 4.86 mmol) in anhydrous dichloromethane (10 mL) was added dropwise over 10 min. The reaction was stirred at ambient temperature for 1.5 h and the mixture was concentrated. Purification by column chromatography, using a gradient of 5-30% ethyl acetate in heptane as the eluent, gave 0.51 g of the title compound.

Workup

  1. customthe cooling bath was removed
  2. stirringThe reaction was stirred at ambient temperature for 1.5 h
  3. concentrationthe mixture was concentrated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-72f2771e10f241ebb4bb5b93b03c56bc
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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