2-(4-Hydroxyphenyl)-5-octylpyrimidine → 5-Octyl-2-[4-(4-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)butoxy)phenyl]pyrimidine
Reaction equation
[F:1][C:2]([F:29])([F:28])[O:3][C:4]([F:27])([F:26])[C:5]([F:25])([F:24])[O:6][C:7]([F:23])([F:22])[C:8]([F:21])([F:20])[O:9][C:10]([F:19])([F:18])[CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.[CH2:30]([C:38]1[CH:39]=[N:40][C:41]([C:44]2[CH:49]=[CH:48][C:47]([OH:50])=[CH:46][CH:45]=2)=[N:42][CH:43]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>>[CH2:30]([C:38]1[CH:43]=[N:42][C:41]([C:44]2[CH:49]=[CH:48][C:47]([O:50][CH2:16][CH2:15][CH2:14][CH2:13][O:12][CH2:11][C:10]([O:9][C:8]([F:20])([F:21])[C:7]([F:22])([F:23])[O:6][C:5]([F:24])([F:25])[C:4]([F:26])([F:27])[O:3][C:2]([F:28])([F:29])[F:1])([F:19])[F:18])=[CH:46][CH:45]=2)=[N:40][CH:39]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared essentially as in Example 1 by combining 4-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromobutane (20.9 g, 38.5 mol; prepared from 1,4-dibromobutane and 2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethanol) with 5-octyl-2-(4-hydroxyphenyl)pyrimidine (10.0 g, 0.35 mol). The resulting product was further purified by recrystallization from ethanol and subsequent Kugelrohr distillation to provide a yield of 17.5 g (b.p. 195-220° C. at 0.1 torr).
Workup
- distillationThe resulting product was further purified by recrystallization from ethanol and subsequent Kugelrohr distillation
- customto provide a yield of 17.5 g (b.p. 195-220° C. at 0.1 torr)
Sources & evidence
- ORD record
- ord-d29aff48d0f84754acf59f3bb858b2ae
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05928562
Reaction notes
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