Phosphorus tribromide → 4-Bromoquinoline-6-carbonitrile

HRID 1782006Notes

Reaction equation

HRID 1782006 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[NH:5][CH:4]=[CH:3]1.P(Br)(Br)[Br:15]>CN(C=O)C.O>[Br:15][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 116583514-Hydroxyquinoline-6-carbonitrile

Product 1

HCID 115214964-Bromoquinoline-6-carbonitrileYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (b) (12 g, 70.5 mmol) in DMF (75 ml) was added dropwise phosphorous tribromide (8 ml, 84.6 mmol) over five minutes (slightly exothermic). The reaction was allowed to cool to room temperature and was then diluted with ice water (100 ml) and stirred 1 hour then diluted with additional water (300 ml). The product was filtered off, washed with water and air dried to provide 14.3 g of product (87%).

Workup

  1. filtrationThe product was filtered off
  2. washwashed with water and air
  3. customdried

Sources & evidence

ORD record
ord-04563999b3a041a0b74bd013cbe3b613
Source dataset
uspto-grants-2009_03
Patent number
US07498326B2

Reaction notes

Loading…