2-(4-Hydroxyphenyl)-5-octylpyrimidine → 5-Octyl-2-[4-(6-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)hexyloxy)phenyl]pyrimidine

HRID 2257474Notes

Reaction equation

HRID 2257474 reaction equation
[F:1][C:2]([F:31])([F:30])[O:3][C:4]([F:29])([F:28])[C:5]([F:27])([F:26])[O:6][C:7]([F:25])([F:24])[C:8]([F:23])([F:22])[O:9][C:10]([F:21])([F:20])[CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[CH2:32]([C:40]1[CH:41]=[N:42][C:43]([C:46]2[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=2)=[N:44][CH:45]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>>[CH2:32]([C:40]1[CH:45]=[N:44][C:43]([C:46]2[CH:51]=[CH:50][C:49]([O:52][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][CH2:11][C:10]([O:9][C:8]([F:22])([F:23])[C:7]([F:24])([F:25])[O:6][C:5]([F:26])([F:27])[C:4]([F:28])([F:29])[O:3][C:2]([F:1])([F:31])[F:30])([F:21])[F:20])=[CH:48][CH:47]=2)=[N:42][CH:41]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

3

Reactant 2

HCID 6040552-(4-Hydroxyphenyl)-5-octylpyrimidineHCID 212253216-(2-(2-(2-(Trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromohexane

Product 1

HCID 212254155-Octyl-2-[4-(6-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)hexyloxy)phenyl]pyrimidine

Procedure

The title compound was prepared essentially as in Example 1 by combining 6-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromohexane (85 g, 0.155 mol; prepared from 1,6-dibromohexane (500 g, 0.7 mol), 10 2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethanol (150 g, 0.37 mol), and potassium t-butoxide (412 mL of 1M solution in t-butanol)) with 5-octyl-2-(4-hydroxyphenyl)pyrimidine (45 g, 0. 162 mol). The crude product was further purified by recrystallization from heptane and subsequently dried in a vacuum oven (yield of 93.0 g).

Workup

  1. customThe crude product was further purified by recrystallization from heptane
  2. customsubsequently dried in a vacuum oven (yield of 93.0 g)

Sources & evidence

ORD record
ord-a93017af0b2e46bda183c22159bd2037
Source dataset
uspto-grants-1997_08
Patent number
US05658491

Reaction notes

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