HCID 20372291, compound → HCID 20372220, compound

HRID 1284279Notes

Reaction equation

HRID 1284279 reaction equation
[CH3:1][C:2]1[C:9]([C:10]([F:21])([F:20])[C:11]([F:19])([F:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[C:22]1(=[O:32])[NH:26][C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.[K]>CN(C)C=O>[CH3:1][C:2]1[C:9]([C:10]([F:21])([F:20])[C:11]([F:19])([F:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:26]1[C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]2[C:22]1=[O:32]

Participants

4

Reactant 2

HCID 20372291HCID 20372291, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 20372220HCID 20372220, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8.02 g. (0.022 mole) of 2-methyl-3-(α,α,β,β-tetrafluorophenethyl)-benzyl bromide, 4.10 g. (0.022 mole) of potassium phthalimide, and 40 ml. of dimethylformamide is stirred 30 minutes at room temperature, 4 hours at 95°C., and 3 hours at reflux. The cooled mixture is diluted with 100 ml. of chloroform and washed with 150 ml. of water. After re-extraction of the aqueous layer with chloroform, the combined organic extracts are washed with 0.1 N. sodium hydroxide, water, dried over anhydrous magnesium sulfate, and evaporated to dryness in vacuo. Recrystallization of the residual solid from isopropyl alchol affords the white crystalline product, m.p. 135°-137°C.

Workup

  1. additionA mixture of 8.02 g
  2. temperature3 hours at reflux
  3. additionThe cooled mixture is diluted with 100 ml
  4. washof chloroform and washed with 150 ml
  5. extractionAfter re-extraction of the aqueous layer with chloroform
  6. washthe combined organic extracts are washed with 0.1 N
  7. dry with materialsodium hydroxide, water, dried over anhydrous magnesium sulfate
  8. customevaporated to dryness in vacuo
  9. customRecrystallization of the residual solid from isopropyl alchol
  10. customaffords the white crystalline product, m.p. 135°-137°C.

Sources & evidence

ORD record
ord-b6cc1dee2d2d4c0cbdf446c4779d00f3
Source dataset
uspto-grants-1976_08
Patent number
US03978127

Reaction notes

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