4-(2-(2-(Pentafluoroethoxy) tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromobutane → 5-Hexyloxy-2-[4-(4-(2-(2-(pentafluoroethoxy) tetrafluoroethoxy)-2,2-difluoroethoxy)butoxy)phenyl]pyrimidine
Reaction equation
[F:1][C:2]([F:25])([O:7][C:8]([F:24])([F:23])[C:9]([F:22])([F:21])[O:10][C:11]([F:20])([F:19])[CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17]Br)[C:3]([F:6])([F:5])[F:4].[CH2:26]([O:32][C:33]1[CH:34]=[N:35][C:36]([C:39]2[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=2)=[N:37][CH:38]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O>[CH2:26]([O:32][C:33]1[CH:38]=[N:37][C:36]([C:39]2[CH:40]=[CH:41][C:42]([O:45][CH2:17][CH2:16][CH2:15][CH2:14][O:13][CH2:12][C:11]([O:10][C:9]([F:22])([F:21])[C:8]([F:24])([F:23])[O:7][C:2]([F:25])([F:1])[C:3]([F:6])([F:5])[F:4])([F:20])[F:19])=[CH:43][CH:44]=2)=[N:35][CH:34]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared essentially as in Example 1 by combining 4-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromobutane (14.9 g, 32.0 mmol, Example 19) with 5-hexyloxy-2-(4-hydroxyphenyl)pyrimidine (8.0 g, 29.4 mmol). The resulting product was isolated by addition of water (160 mL), 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. 190°-205° C. at 0.3 torr; yield of 15.2 g).
Workup
- filtrationfollowed by filtration and recrystallization from ethanol
- customThe recrystallized precipitate was dried at about 130° C.
- distillationthe resulting product was further purified by distillation
Sources & evidence
- ORD record
- ord-d99b50276f714a63a587392a8bb2d595
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05658491
Reaction notes
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