Potassium Iodide → N-[4-bromo-3-(1-ethoxycarbonylbutyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

HRID 485200Notes

Reaction equation

HRID 485200 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[OH:19].Br[CH:21]([CH2:27][CH2:28][CH3:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9](=[O:18])[C:10]3[CH2:17][CH2:16][CH2:15][CH2:14][C:11]=3[C:12]2=[O:13])=[CH:4][C:3]=1[O:19][CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79071Ethyl 2-bromovalerateHCID 12769237N-(4-bromo-3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide

Product 1

HCID 15582848N-[4-bromo-3-(1-ethoxycarbonylbutyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 15.0 g. of N-(4-bromo-3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide, 12.0 g. of ethyl α-bromovalerate, 7.7 g. of potassium carbonate, 2.5 g. of potassium iodide and 50 ml. of acetone was refluxed with stirring for 3 hours and then, the reaction mixture was cooled to room temperature and the salt was separated by a filtration. The filtrate was concentrated under a reduced pressure and 2N-HCl was added to the residue to crystallize the product. The crystal was separated by a filtration and washed with water and dried. The residue was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate: n-hexane of 1:3) to obtain 17.6 g. of Compound No. 90 shown in table 1.

Workup

  1. additionA mixture of 15.0 g
  2. customthe salt was separated by a filtration
  3. concentrationThe filtrate was concentrated under a reduced pressure and 2N-HCl
  4. additionwas added to the residue
  5. customto crystallize the product
  6. customThe crystal was separated by a filtration
  7. washwashed with water
  8. customdried
  9. customThe residue was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate: n-hexane of 1:3)
  10. customto obtain 17.6 g

Sources & evidence

ORD record
ord-4de79521328748efa30b11fa01c2c1d5
Source dataset
uspto-grants-1985_08
Patent number
US04536209

Reaction notes

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