Phosphorus oxybromide → 4-Bromo-7-chloroquinoline

HRID 234697Notes

Reaction equation

HRID 234697 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.P(Br)(Br)([Br:15])=O>>[Br:15][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178516426HCID 178516426, compound

Product 1

HCID 109776384-Bromo-7-chloroquinoline

Conditions

Temperature
140 °C

Procedure

83.9 g of 7-chloro-4-hydroxyquinoline were added portionwise at 60° to 150 g of phosphorus oxybromide and the mixture was thereafter heated to 140° C. for 6 hours. After cooling, the mixture was treated with 3 l of ice-water and extracted with 2×1.5 l of dichloromethane. After evaporation of the solvent and crystallization from 1.3 l of hexane, 34 g of product were obtained as colourless crystals, m.p.: 102°-103° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 2×1.5 l of dichloromethane
  3. customAfter evaporation of the solvent and crystallization from 1.3 l of hexane

Sources & evidence

ORD record
ord-3e37bc2166914a44b1c27ccc5b2660e2
Source dataset
uspto-grants-1997_01
Patent number
US05596002

Reaction notes

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