Phosphorus oxychloride → 7-Bromo-4-chloro-8-methylquinoline

HRID 1473532Notes

Reaction equation

HRID 1473532 reaction equation
[Br:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](O)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:16]>C(#N)C>[Br:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6]([Cl:16])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178421692HCID 178421692, compound

Product 1

HCID 455993807-Bromo-4-chloro-8-methylquinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a flask charged with 7-bromo-8-methylquinolin-4-ol (1.00 g, 4.20 mmol) was added Acetonitrile (21.00 ml) and POCl3 (0.411 ml, 4.41 mmol) and the resulting suspension heated to 90° C. for 1.5 hrs affording a brown solution and near complete conversion to desired product. The mixture was added to a cooled solution of sat. aq. NaHCO3 affording a tan precipitate which was collected via vacuum filtration and washed with water and dried under high vacuum affording product as a tan solid. m/z (ESI) 258.0 (M+H)+.

Workup

  1. customaffording a brown solution

Sources & evidence

ORD record
ord-6b310edba67b4b4fafc7e696a640da95
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

Loading…