Phenacyl bromide → HCID 15582984, compound

HRID 485205Notes

Reaction equation

HRID 485205 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[O:19][CH:20]([C:24]([OH:26])=[O:25])[CH2:21][CH2:22][CH3:23].[CH2:27](Br)[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].[F-].[K+]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[O:19][CH:20]([C:24]([O:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29])=[O:25])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 522689Potassium FluorideHCID 13503453HCID 13503453, compound

Product 1

HCID 15582984HCID 15582984, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.11 g. of N-[4-bromo-3-(1-carboxybutyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide, 11.19 g. of phenacyl bromide, 0.64 g. of potassium fluoride and 10 ml. of acetonitrile was refluxed with stirring for 8.5 hours and the reaction mixture was cooled and the precipitate was separated by a filtration. The filtrate was concentrated under a reduced pressure and the residue was purified by a chromatography on a column of silica gel (developing solvent of benzene) to obtain 2.20 g. of Compound No. 141 shown in Table 1.

Workup

  1. additionA mixture of 2.11 g
  2. temperaturethe reaction mixture was cooled
  3. customthe precipitate was separated by a filtration
  4. concentrationThe filtrate was concentrated under a reduced pressure
  5. customthe residue was purified by a chromatography on a column of silica gel (developing solvent of benzene)
  6. customto obtain 2.20 g

Sources & evidence

ORD record
ord-f90509e0c3714a23bf2e730e67be18ed
Source dataset
uspto-grants-1985_08
Patent number
US04536209

Reaction notes

Loading…