Potassium Iodide → N-(2-Fluoro-5-isopropoxyphenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1284610Notes

Reaction equation

HRID 1284610 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](Br)([CH3:22])[CH3:21].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C)C=O>[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

7

Reactant 4

HCID 4875Potassium IodideHCID 63582-BromopropaneHCID 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 99.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

N-(2-Fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (VI) (20 g), isopropyl bromide (25 g), potassium iodide (5 g) and anhydrous potassium carbonate (11 g) were dissolved in a mixture of acetonitrile (135 g) and dimethylformamide (15 g), and the resultant solution was heated under reflux for 7 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 23.2 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 7 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-416147f2c2f94b9bbd039c9341779d62
Source dataset
uspto-grants-1986_01
Patent number
US04563535

Reaction notes

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