Phosphorus oxychloride → HCID 21578662, compound

HRID 1294639Notes

Reaction equation

HRID 1294639 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[CH:6]=[C:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1.P(Cl)(Cl)([Cl:22])=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:22])[CH:6]=[C:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12016671HCID 12016671, compound

Product 1

HCID 21578662HCID 21578662, compoundYield 100%

Procedure

A mixture of intermediate 4 (0.16 mol) in phosphoryl chloride (500ml) was stirred and refluxed for one night. The mixture was evaporated till dryness, the residue was taken up in ice and water, alkalized with NH4OH and extracted with DCM. The organic layer was decanted, dried (MgSO4), filtered off and evaporated, yielding 56 g (100%) of 6-bromo-2-chloro-4-(3-chlorophenyl)quinoline, mp.125° C. (intermediate 5).

Workup

  1. temperaturerefluxed for one night
  2. customThe mixture was evaporated till dryness
  3. extractionextracted with DCM
  4. customThe organic layer was decanted
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered off
  7. customevaporated

Sources & evidence

ORD record
ord-4e97dd3d38d4430bb388d25660484d11
Source dataset
uspto-grants-2007_07
Patent number
US07241777B2

Reaction notes

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