5-Bromovaleryl chloride → HCID 22252386, compound

HRID 1611995Notes

Reaction equation

HRID 1611995 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[CH:7]=1)CCC.[Br:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](Cl)=[O:32]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Br:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([C:6]1[CH:7]=[C:8]([O:16][CH3:17])[C:9]([O:14][CH3:15])=[C:10]([O:12][CH3:13])[CH:11]=1)=[O:32]

Participants

5

Reactant 2

HCID 5211735-Bromovaleryl chlorideHCID 10072789HCID 10072789, compound

Product 1

HCID 22252386HCID 22252386, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of 8.5 g of the compound obtained in Step A, 3.2 ml of 5-bromopentanoyl chloride, 0.3 g of Pd2(dba)3 and 250 ml of toluene is refluxed for 6 hours, and then cooled and evaporated in vacuo. The residue is purified by chromatography over silica gel eluted with dichloromethane, enabling the expected product to be isolated.

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. customThe residue is purified by chromatography over silica gel
  4. washeluted with dichloromethane
  5. customto be isolated

Sources & evidence

ORD record
ord-cacb20fdd933418fbe595f1f586c6532
Source dataset
uspto-grants-2006_01
Patent number
US06992085B2

Reaction notes

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