2-(4-Hydroxyphenyl)-5-octylpyrimidine → 5-Octyl-2-[4-(3-(4-(2-(trifluoromethoxy)tetrafluoroethoxy)-2,2,3,3,4,4-hexafluorobutoxy)propoxy)phenyl]pyrimidine
Reaction equation
[F:1][C:2]([F:27])([F:26])[O:3][C:4]([F:25])([F:24])[C:5]([F:23])([F:22])[O:6][C:7]([F:21])([F:20])[C:8]([F:19])([F:18])[C:9]([F:17])([F:16])[CH2:10][O:11][CH2:12][CH2:13][CH2:14]Cl.FC(F)(F)OC(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)COCCCBr.[CH2:55]([C:63]1[CH:64]=[N:65][C:66]([C:69]2[CH:74]=[CH:73][C:72]([OH:75])=[CH:71][CH:70]=2)=[N:67][CH:68]=1)[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62]>>[CH2:55]([C:63]1[CH:68]=[N:67][C:66]([C:69]2[CH:74]=[CH:73][C:72]([O:75][CH2:14][CH2:13][CH2:12][O:11][CH2:10][C:9]([F:17])([F:16])[C:8]([F:19])([F:18])[C:7]([O:6][C:5]([F:23])([F:22])[C:4]([F:25])([F:24])[O:3][C:2]([F:27])([F:26])[F:1])([F:21])[F:20])=[CH:71][CH:70]=2)=[N:65][CH:64]=1)[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62]Participants
Reactant 3
Product 1
Procedure
The title compound was prepared essentially as in Example 1 by combining a mixture of 3-(4-(2-(trifluoromethoxy)tetrafluoroethoxy)-2,2,3,3,4,4-hexafluorobutoxy)propyl chloride (1.92 g, 4.2 mmol) and 3-(4-(2-(trifluoromethoxy)tetrafluoroethoxy)-2,2,3,3,4,4-hexafluorobutoxy)propyl bromide (4:1 mole ratio, total 0.87 g, 1.7 mmol, prepared from 1-bromo-3-chloropropane and 4-(2-(trifluoromethoxy)tetrafluoroethoxy)-2,2,3,3,4,4-hexafluorobutanol) with 5-octyl-2-(4-hydroxyphenyl)pyrimidine (1.6 g, 5.9 mmol). The resulting crude product was isolated essentially as described in Example 3 and purified by chromatography on silica gel, eluting with 10 vol. % ethyl acetate in hexane, followed by Kugelrohr distillation (230° C. at 0.4 torr) to provide a yield of 2 g.
Sources & evidence
- ORD record
- ord-8e27e17323ff4ae79344028846a2fc9c
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05928562
Reaction notes
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