3-(2-(2-(2-(Trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl chloride → 2-Octyloxy-7-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)fluorene

HRID 582996Notes

Reaction equation

HRID 582996 reaction equation
[CH2:1]([O:9][C:10]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[CH:15][C:16]([OH:23])=[CH:17][CH:18]=3)[CH2:13][C:12]=2[CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[F:24][C:25]([F:51])([F:50])[O:26][C:27]([F:49])([F:48])[C:28]([F:47])([F:46])[O:29][C:30]([F:45])([F:44])[C:31]([F:43])([F:42])[O:32][C:33]([F:41])([F:40])[CH2:34][O:35][CH2:36][CH2:37][CH2:38]Cl.FC(F)(F)OC(F)(F)C(F)(F)OC(F)(F)C(F)(F)OC(F)(F)COCCCBr>>[CH2:1]([O:9][C:10]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH2:38][CH2:37][CH2:36][O:35][CH2:34][C:33]([O:32][C:31]([F:42])([F:43])[C:30]([F:44])([F:45])[O:29][C:28]([F:46])([F:47])[C:27]([F:48])([F:49])[O:26][C:25]([F:51])([F:50])[F:24])([F:41])[F:40])=[CH:17][CH:18]=3)[CH2:13][C:12]=2[CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 212252903-(2-(2-(2-(Trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl chlorideHCID 212253953-(2-(2-(2-(Trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl bromideHCID 218324622-Octyloxy-7-hydroxyfluorene

Product 1

HCID 212253882-Octyloxy-7-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)fluorene

Procedure

The title compound was prepared essentially as in Example 1 by combining 2-octyloxy-7-hydroxyfluorene (1.0 g, 3.2 mmol) with a mixture of 3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl chloride and 3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl bromide (total 1.62 g, 3.3 mmol, 80:20 mole ratio). The reaction mixture was quenched by addition of water, and the resulting crude product was recrystallized from ethanol and further purified by Kugelrohr distillation (188° C. at 0.01 torr) to provide a yield of 0.84 g.

Workup

  1. customThe reaction mixture was quenched by addition of water
  2. customthe resulting crude product was recrystallized from ethanol
  3. distillationfurther purified by Kugelrohr distillation (188° C. at 0.01 torr)
  4. customto provide a yield of 0.84 g

Sources & evidence

ORD record
ord-40f70ba16887488aaec23fbd3dbdc9e5
Source dataset
uspto-grants-1999_07
Patent number
US05928562

Reaction notes

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