Phosphorus tribromide → HCID 60207313, compound

HRID 1192054Notes

Reaction equation

HRID 1192054 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[S:14][C:13]([CH:15](O)[CH3:16])=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19].[Br:21]P(Br)Br>ClCCl>[Br:21][CH:15]([C:13]1[S:14][C:10]([S:9][C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[C:11]([N+:18]([O-:20])=[O:19])[CH:12]=1)[CH3:16]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 46932149HCID 46932149, compound

Product 1

HCID 60207313HCID 60207313, compoundYield 113.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[5-(2,4-dichlorophenyl)sulfanyl-4-nitro-2-thienyl]ethanol from example 26 (0.6 g, 1.7 mmol) in dichloromethane (10 mL), was added tribromophosphane (0.28 mL, 2.55 mmol). The resulting reaction mixture was kept under reflux for 2 hours. After this time, the reaction mixture was cooled to ambient temperature, quenched with sat'd sodium carbonate aqueous solution and extracted with ethyl acetate. The combined organic phase was dried (Na2SO4) and concentrated to afford the title compound (800 mg). The crude product was used as such for the next step.

Workup

  1. customThe resulting reaction mixture
  2. temperatureunder reflux for 2 hours
  3. customquenched with sat'd sodium carbonate aqueous solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phase was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2ff27a32ac74454abc490c7171903f2f
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

Loading…