5-(2-(2-(Pentafluoroethoxy) tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromopentane → 5-Hexyloxy-2-[4-(5-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)pentyloxy)phenyl]pyrimidine

HRID 2257470Notes

Reaction equation

HRID 2257470 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:46])([O:27][C:28]([F:45])([F:44])[C:29]([F:43])([F:42])[O:30][C:31]([F:41])([F:40])[CH2:32][O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Br)[C:23]([F:26])([F:25])[F:24]>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][O:33][CH2:32][C:31]([O:30][C:29]([F:42])([F:43])[C:28]([F:44])([F:45])[O:27][C:22]([F:21])([F:46])[C:23]([F:24])([F:25])[F:26])([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 212253685-(2-(2-(Pentafluoroethoxy) tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromopentaneHCID 1361744305-Hexyloxy-2-(4-hydroxyphenyl)pyrimidine

Product 1

HCID 212253415-Hexyloxy-2-[4-(5-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)pentyloxy)phenyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared essentially as in Example 1 by combining 5-hexyloxy-2-(4-hydroxyphenyl)pyrimidine (2.26 g, 8.3 mmol) with 5-(2-(2-(pentafluoroethoxy) tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromopentane (4.08 g, 8.3 mmol; prepared by combining 1,5-dibromopentane with 2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethanol). Product was isolated by addition of water (160 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. 190°-205° C. at 0.3 torr; yield of 15.2 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. 190°-205° C. at 0.3 torr; yield of 15.2 g)

Sources & evidence

ORD record
ord-501d5e08ed15449da852629551526f6a
Source dataset
uspto-grants-1997_08
Patent number
US05658491

Reaction notes

Loading…