Phosphorus oxybromide → 2,8-Dibromoquinoline

HRID 1095668

Reaction equation

HRID 1095668 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=O)[CH:8]=[CH:7]2.P(Br)(Br)([Br:15])=O>O>[Br:15][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([Br:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 109330948-Bromo-1,2-dihydroquinolin-2-one

Product 1

HCID 459259512,8-DibromoquinolineYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 8-bromoquinolin-2(1H)-one (5 g, 22 mmol) and phosphoryl tribromide (13 g, 45 mmol) was heated to 140° C. for three hours. The resulting mixture was poured onto 100 g of ice and 100 ml water. The mixture was stirred for 1 hour and the resulting solids were filtered to yield the title compound. (5.1 g, 80% yield) MS APCI (+) 286, 288, and 290 (M+1 of each isotope combination) detected.

Workup

  1. filtrationthe resulting solids were filtered

Sources & evidence

ORD record
ord-f295163c5eb74fd1b7e6855b6c336ce1
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Linked notes

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