2-(2-(2-(2-(Nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)ethoxy)ethyl bromide → 5-Hexyloxy-2-[4-(2-(2-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)ethoxy)ethoxy)phenyl]pyrimidine

HRID 2257464Notes

Reaction equation

HRID 2257464 reaction equation
[F:1][C:2]([F:32])([C:28]([F:31])([F:30])[F:29])[C:3]([F:27])([F:26])[C:4]([F:25])([F:24])[O:5][C:6]([F:23])([F:22])[C:7]([F:21])([F:20])[O:8][C:9]([F:19])([F:18])[CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16]Br.[CH2:33]([O:39][C:40]1[CH:41]=[N:42][C:43]([C:46]2[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=2)=[N:44][CH:45]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>O>[CH2:33]([O:39][C:40]1[CH:45]=[N:44][C:43]([C:46]2[CH:47]=[CH:48][C:49]([O:52][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][C:9]([O:8][C:7]([F:21])([F:20])[C:6]([F:23])([F:22])[O:5][C:4]([F:25])([F:24])[C:3]([F:27])([F:26])[C:2]([F:32])([F:1])[C:28]([F:31])([F:30])[F:29])([F:19])[F:18])=[CH:50][CH:51]=2)=[N:42][CH:41]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 2

HCID 212253182-(2-(2-(2-(Nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)ethoxy)ethyl bromideHCID 1361744305-Hexyloxy-2-(4-hydroxyphenyl)pyrimidine

Product 1

HCID 212253275-Hexyloxy-2-[4-(2-(2-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)ethoxy)ethoxy)phenyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared essentially as in Example 1 by combining 2-(2-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)ethoxy)ethyl bromide (7.7 g of 90% purity by gas chromatography 11.8 mmol) with 5-hexyloxy-2-(4-hydroxyphenyl)pyrimidine (3.0 g, 11.0 mmol). The resulting product was isolated by addition of water (50 mL) to the reaction mixture, followed by filtration and recrystallization from ethanol. The recrystallized precipitate was dried at about 130° C., and the resulting product was further purified by distillation using a Kugelrohr apparatus (b.p. 185°-210° C. at 0.01 torr; yield 5.6 g).

Workup

  1. filtrationfollowed by filtration and recrystallization from ethanol
  2. customThe recrystallized precipitate was dried at about 130° C.
  3. distillationthe resulting product was further purified by distillation

Sources & evidence

ORD record
ord-6645d8b4b9cf4e789caeb98c994a51ee
Source dataset
uspto-grants-1997_08
Patent number
US05658491

Reaction notes

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