2-(4-Hydroxyphenyl)-5-octylpyrimidine → 5-Octyl-2-[4-(5-(2-(nonafluorobutoxy)-2,2-difluoroethoxy)pentyloxy)phenyl]pyrimidine

HRID 2257480Notes

Reaction equation

HRID 2257480 reaction equation
[CH2:1]([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][CH2:7][CH3:8].[F:22][C:23]([F:46])([C:42]([F:45])([F:44])[F:43])[C:24]([F:41])([F:40])[C:25]([F:39])([F:38])[O:26][C:27]([F:37])([F:36])[CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]Br>>[CH2:1]([C:9]1[CH:14]=[N:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][O:29][CH2:28][C:27]([O:26][C:25]([F:38])([F:39])[C:24]([F:40])([F:41])[C:23]([F:22])([F:46])[C:42]([F:43])([F:44])[F:45])([F:37])[F:36])=[CH:17][CH:16]=2)=[N:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 6040552-(4-Hydroxyphenyl)-5-octylpyrimidineHCID 21225329HCID 21225329, compound

Product 1

HCID 212253805-Octyl-2-[4-(5-(2-(nonafluorobutoxy)-2,2-difluoroethoxy)pentyloxy)phenyl]pyrimidine

Procedure

The title compound was prepared essentially as in Example 1 by combining 5-octyl-2-(4-hydroxyphenyl)pyrimidine (6.0 g, 21 mmol) and 5-(2-(nonafluorobutoxy)-2,2-difluoroethoxy)-1-bromopentane (12 g, 23 mmol; prepared by combining 1,5-dibromopentane with 2-(nonafluorobutoxy)-2,2-difluoroethanol). After refluxing overnight, the resulting crude product was isolated by filtration and further purified by recrystallization from ethanol, followed by Kugelrohr distillation (b.p. 190°-200° C. at 0.1 torr; yield of 6.4 g).

Workup

  1. temperatureAfter refluxing overnight

Sources & evidence

ORD record
ord-ba85ec9f375f454e80712e694e9f683d
Source dataset
uspto-grants-1997_08
Patent number
US05658491

Reaction notes

Loading…