3-(2-(2-(Nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl bromide → 4-Decyloxy-4'-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyloxy)tolane
Reaction equation
[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[F:27][C:28]([F:56])([C:52]([F:55])([F:54])[F:53])[C:29]([F:51])([F:50])[C:30]([F:49])([F:48])[O:31][C:32]([F:47])([F:46])[C:33]([F:45])([F:44])[O:34][C:35]([F:43])([F:42])[CH2:36][O:37][CH2:38][CH2:39][CH2:40]Br>>[CH2:1]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:40][CH2:39][CH2:38][O:37][CH2:36][C:35]([O:34][C:33]([F:44])([F:45])[C:32]([F:46])([F:47])[O:31][C:30]([F:48])([F:49])[C:29]([F:50])([F:51])[C:28]([F:27])([F:56])[C:52]([F:55])([F:54])[F:53])([F:43])[F:42])=[CH:22][CH:21]=2)=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]Participants
3
Procedure
The title compound was prepared essentially as in Example 1 by combining 4-decyloxy-4'-hydroxytolane (1.5 g, 4.3 mmol, prepared essentially as described in EP 641850) with 3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl bromide (2.6 g, 4.7 mmol). The reaction mixture was quenched with water, and the resulting crude product was further purified by recrystallization from ethanol, followed by Kugelrohr distillation (200-220° C. at 0.5 torr), to provide a yield of 2.64 g.
Workup
- customprepared essentially
- customThe reaction mixture was quenched with water
- customthe resulting crude product was further purified by recrystallization from ethanol
- distillationfollowed by Kugelrohr distillation (200-220° C. at 0.5 torr)
- customto provide a yield of 2.64 g
Sources & evidence
- ORD record
- ord-febb62542f0a4517b0c06e280eee1265
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05928562
Reaction notes
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