tert-Butyl methyl ether → 4-(5-Octyl pyrimidine-2-yl)phenyl nonafluorobutane sulfonate

HRID 378204Notes

Reaction equation

HRID 378204 reaction equation
[CH2:1]([C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[F:22][C:23]([F:38])([S:34](F)(=[O:36])=[O:35])[C:24]([F:33])([F:32])[C:25]([F:31])([F:30])[C:26]([F:29])([F:28])[F:27].C(OC)(C)(C)C>O>[F:29][C:26]([F:27])([F:28])[C:25]([F:30])([F:31])[C:24]([F:32])([F:33])[C:23]([F:38])([F:22])[S:34]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][N:13]=2)=[CH:16][CH:17]=1)(=[O:35])=[O:36]

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 6040552-(4-Hydroxyphenyl)-5-octylpyrimidine

Product 1

HCID 542376574-(5-Octyl pyrimidine-2-yl)phenyl nonafluorobutane sulfonateYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
16 °C

Procedure

A 12 liter flask fitted with a mechanical stirrer, a constant addition funnel, a thermometer, and a reflux condenser was charged with of 5-octyl-2-(4-hydroxyphenyl)pyrimidine (300 g, 1.05 mol), perfluorobutanesulfonyl fluoride (378 g, 1.25 mol), and tert-butylmethylether (3 L) under positive nitrogen pressure and was cooled with an ice bath to 16° C. 1,8-Diazobicyclo[5.4.0]undec-7-ene (180 g, 1.18 mol) was added to the resulting mixture over 25 minutes, while maintaining the temperature of the mixture below 20° C. After the addition was complete, the mixture was stirred at room temperature for 2 hours, and then 3 liters of water was added. The resulting aqueous phase was separated from the resulting organic phase, and the organic phase was washed with a mixture of 2.25 liters of water and 0.75 liters of concentrated HCl. The solvent was removed from the organic phase under reduced pressure to yield 697 g of crude product, which was recrystallized from ethanol to yield 4-(5-octyl pyrimidine-2-yl)phenyl nonafluorobutane sulfonate (499 g, 84% yield).

Workup

  1. customA 12 liter flask fitted with a mechanical stirrer, a constant addition funnel
  2. temperaturewhile maintaining the temperature of the mixture below 20° C
  3. additionAfter the addition
  4. customThe resulting aqueous phase was separated from the resulting organic phase
  5. washthe organic phase was washed with a mixture of 2.25 liters of water and 0.75 liters of concentrated HCl
  6. customThe solvent was removed from the organic phase under reduced pressure
  7. customto yield 697 g of crude product, which
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-96dff28941ad4494b1e9c9f066b46add
Source dataset
uspto-grants-2000_02
Patent number
US06030547

Reaction notes

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