3-(2-(2-(Nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl bromide → 5-Heptyloxy-2-[4-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine

HRID 2257457Notes

Reaction equation

HRID 2257457 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[F:22][C:23]([F:51])([C:47]([F:50])([F:49])[F:48])[C:24]([F:46])([F:45])[C:25]([F:44])([F:43])[O:26][C:27]([F:42])([F:41])[C:28]([F:40])([F:39])[O:29][C:30]([F:38])([F:37])[CH2:31][O:32][CH2:33][CH2:34][CH2:35]Br>O>[CH2:1]([O:8][C:9]1[CH:14]=[N:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:35][CH2:34][CH2:33][O:32][CH2:31][C:30]([O:29][C:28]([F:39])([F:40])[C:27]([F:41])([F:42])[O:26][C:25]([F:43])([F:44])[C:24]([F:45])([F:46])[C:23]([F:22])([F:51])[C:47]([F:50])([F:49])[F:48])([F:38])[F:37])=[CH:19][CH:20]=2)=[N:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 218324923-(2-(2-(Nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl bromideHCID 1357088125-Heptyloxy-2-(4-hydroxyphenyl)pyrimidine

Product 1

HCID 212252955-Heptyloxy-2-[4-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared essentially as described in Example 1 by combining 5-heptyloxy-2-(4-hydroxyphenyl)pyrimidine (3.0 g, 10.0 mmol) and 3-(2-(2-(nonafluorobutoxy) tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromopropane (6.6 g, 12.0 mmol, Example 10). The product was isolated by addition of water (60 mL) to the resulting 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 Kugelrohr distillation (b.p. 180°-190° C. at 2 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 Kugelrohr distillation (b.p. 180°-190° C. at 2 torr; yield 5.6 g)

Sources & evidence

ORD record
ord-178e2aa4740c4febb9710b6c027ae0f1
Source dataset
uspto-grants-1997_08
Patent number
US05658491

Reaction notes

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