7-(2-(2-(Nonafluorobutoxy) tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromoheptane → 5-Hexyloxy-2-[4-(7-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)heptyloxy)phenyl]pyrimidine

HRID 582960Notes

Reaction equation

HRID 582960 reaction equation
[CH2:1]([O:7][C:8]1[CH:9]=[N:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[N:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F:21][C:22]([F:54])([C:50]([F:53])([F:52])[F:51])[C:23]([F:49])([F:48])[C:24]([F:47])([F:46])[O:25][C:26]([F:45])([F:44])[C:27]([F:43])([F:42])[O:28][C:29]([F:41])([F:40])[CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Br>O>[CH2:1]([O:7][C:8]1[CH:13]=[N:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][O:31][CH2:30][C:29]([O:28][C:27]([F:42])([F:43])[C:26]([F:44])([F:45])[O:25][C:24]([F:46])([F:47])[C:23]([F:48])([F:49])[C:22]([F:21])([F:54])[C:50]([F:52])([F:53])[F:51])([F:41])[F:40])=[CH:18][CH:19]=2)=[N:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 212253057-(2-(2-(Nonafluorobutoxy) tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromoheptaneHCID 1361744305-Hexyloxy-2-(4-hydroxyphenyl)pyrimidine

Product 1

HCID 212253315-Hexyloxy-2-[4-(7-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)heptyloxy)phenyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared essentially as described in Example 1 by combining 5-hexyloxy-2-(4-hydroxyphenyl)pyrimidine (3.0 g, 11.0 mmol) and 7-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromoheptane (7.7 g, 12.0 mmol; prepared by combining 1,7-dibromoheptane with 2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethanol). Product was isolated by addition of water (50 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. 210-222° C. at 0.03 torr; yield 7.3 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. 210-222° C. at 0.03 torr; yield 7.3 g)

Sources & evidence

ORD record
ord-b5e6ffd4a4d1487eba39a2ea5f2fb71c
Source dataset
uspto-grants-1999_07
Patent number
US05928562

Reaction notes

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