3-(2-(2-(Pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl bromide → 5-Octyloxy-2-[4-(3-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine
Reaction equation
[F:1][C:2]([F:24])([O:7][C:8]([F:23])([F:22])[C:9]([F:21])([F:20])[O:10][C:11]([F:19])([F:18])[CH2:12][O:13][CH2:14][CH2:15][CH2:16]Cl)[C:3]([F:6])([F:5])[F:4].FC(F)(OC(F)(F)C(F)(F)OC(F)(F)COCCCBr)C(F)(F)F.[CH2:49]([O:57][C:58]1[CH:59]=[N:60][C:61]([C:64]2[CH:69]=[CH:68][C:67]([OH:70])=[CH:66][CH:65]=2)=[N:62][CH:63]=1)[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]>>[CH2:49]([O:57][C:58]1[CH:63]=[N:62][C:61]([C:64]2[CH:65]=[CH:66][C:67]([O:70][CH2:16][CH2:15][CH2:14][O:13][CH2:12][C:11]([O:10][C:9]([F:21])([F:20])[C:8]([F:23])([F:22])[O:7][C:2]([F:24])([F:1])[C:3]([F:6])([F:5])[F:4])([F:19])[F:18])=[CH:68][CH:69]=2)=[N:60][CH:59]=1)[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared essentially as in Example 1 by combining a mixture of 3-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl chloride and 3-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl bromide (75:25 mole ratio, total 4.18 g, 10 mmol, Example 20) with 5-octyloxy-2-(4-hydroxyphenyl)pyrimidine (3.18 g, 10.0 mmol). The resulting crude product was purified by recrystallization from ethanol followed by Kugelrohr distillation (240° C. at 0.4 torr) to provide a yield of 4.3 g.
Workup
- customThe resulting crude product was purified by recrystallization from ethanol
- distillationfollowed by Kugelrohr distillation (240° C. at 0.4 torr)
- customto provide a yield of 4.3 g
Sources & evidence
- ORD record
- ord-c395270348ee426c86717476eb996283
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05928562
Reaction notes
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