Isopropyl iodide → N-(2-Fluoro-5-isopropoxyphenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1284609Notes

Reaction equation

HRID 1284609 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[C:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]=2[C:10]1=[O:19].[CH:20](I)([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:20]([CH3:22])[CH3:21])=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[C:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]=2[C:10]1=[O:19]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 13519181N-(2-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide

Product 1

HCID 13556385N-(2-Fluoro-5-isopropoxyphenyl)-3,4,5,6-tetrahydrophthalimideYield 77.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(2-Fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (VI) (10 g), isopropyl iodide (7 g) and anhydrous potassium carbonate (5.2 g) were dissolved in acetonitrile (100 ml), and the resultant solution was heated under reflux for 2.5 hours. After cooling, the reaction mixture was extracted with ethyl acetate. The extract was concentrated, and the precipitated crystals were collected by filtration to give 9 g of N-(2-fluoro-5-isopropoxyphenyl)-3,4,5,6-tetrahydrophthalimide (II: R=isopropyl). M.P. 62.8° C.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. concentrationThe extract was concentrated
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-e0cc733b4d1e4119ac076070b0f760a5
Source dataset
uspto-grants-1986_01
Patent number
US04563535

Reaction notes

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