3-(2-(2-(Nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl bromide → 5-Octyloxy-2-[4-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyloxy)-2-fluorophenyl)pyrimidine

HRID 583000Notes

Reaction equation

HRID 583000 reaction equation
[CH2:1]([O:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=2[F:23])=[N:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[F:24][C:25]([F:53])([C:49]([F:52])([F:51])[F:50])[C:26]([F:48])([F:47])[C:27]([F:46])([F:45])[O:28][C:29]([F:44])([F:43])[C:30]([F:42])([F:41])[O:31][C:32]([F:40])([F:39])[CH2:33][O:34][CH2:35][CH2:36][CH2:37]Br>>[CH2:1]([O:9][C:10]1[CH:15]=[N:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:37][CH2:36][CH2:35][O:34][CH2:33][C:32]([O:31][C:30]([F:41])([F:42])[C:29]([F:43])([F:44])[O:28][C:27]([F:45])([F:46])[C:26]([F:47])([F:48])[C:25]([F:24])([F:53])[C:49]([F:52])([F:51])[F:50])([F:40])[F:39])=[CH:18][C:17]=2[F:23])=[N:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 218324923-(2-(2-(Nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl bromideHCID 1358568185-Octyloxy-2-[4-hydroxy-2-fluorophenyl)pyrimidine

Product 1

HCID 212253555-Octyloxy-2-[4-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyloxy)-2-fluorophenyl)pyrimidine

Procedure

The title compound was prepared essentially as in Example 1 by combining 5-octyloxy-2-[4-hydroxy-2-fluorophenyl)pyrimidine (1.5 g, 4.7 mmol, prepared from 2-fluoro-4-hydroxybenzamidine hydrobromide and (CH3)2NCH=C(OC8H17)CHO) with 3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl bromide (3.0 g, 5.4 mmol, Example 3). The reaction mixture was quenched with water, and the resulting crude product was further purified by recrystallization from ethanol, followed by Kugelrohr distillation (190-210° C. at 0.5 torr), to provide a yield of 2.85 g.

Workup

  1. customThe reaction mixture was quenched with water
  2. customthe resulting crude product was further purified by recrystallization from ethanol
  3. distillationfollowed by Kugelrohr distillation (190-210° C. at 0.5 torr)
  4. customto provide a yield of 2.85 g

Sources & evidence

ORD record
ord-0651762090b0496d9101eeac7eb4885b
Source dataset
uspto-grants-1999_07
Patent number
US05928562

Reaction notes

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