Water → 1H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-(1-methylethoxy)phenyl)-4,5,6,7-tetrahydro-

HRID 1388550Notes

Reaction equation

HRID 1388550 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[C:12]3[CH2:15][CH2:16][CH2:17][CH2:18][C:11]=3[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:27](I)([CH3:29])[CH3:28].O>CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][CH:27]([CH3:29])[CH3:28])=[CH:6][C:5]([N:9]2[C:10](=[O:19])[C:11]3[CH2:18][CH2:17][CH2:16][CH2:15][C:12]=3[C:13]2=[O:14])=[C:4]([F:20])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 1586511H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-

Product 1

HCID 1586501H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-(1-methylethoxy)phenyl)-4,5,6,7-tetrahydro-Yield 35.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-chloro-2-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (2.95 g) in dimethylformamide (20 ml), there was added anhydrous potassium carbonate (0.8 g) while stirring at room temperature. After stirring for 10 minutes at about 40° C., isopropyl iodide (1.7 g) was added thereto, and the resultant mixture was stirred for 3 hours at 70°-80° C. After being allowed to cool to room temperature, the mixture was poured into water and extracted with toluene. The toluene layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography to obtain 1.2 g of N-(4-chloro-2-fluoro-5-isopropoxyphenyl)3,4,5,6-tetrahydrophthalimide (Compound No. 1). M.P., 81°-82° C.

Workup

  1. stirringAfter stirring for 10 minutes at about 40° C.
  2. temperatureto cool to room temperature
  3. extractionextracted with toluene
  4. washThe toluene layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-74628bcd1f8243b6b486a4be33d1a63b
Source dataset
uspto-grants-1984_02
Patent number
US04431822

Reaction notes

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