Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof
US-2017159088-A1 · Jun 8, 2017 · US
US9790150B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9790150-B2 |
| Application number | US-201514813415-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jul 30, 2015 |
| Priority date | Aug 12, 2014 |
| Publication date | Oct 17, 2017 |
| Grant date | Oct 17, 2017 |
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Processes for producing branched fluoroalkyl olefins are disclosed. In addition, novel halo-fluoroalkane intermediates are disclosed that may be used in the branched fluoroalkyl olefin production processes. Non-limiting examples of branched fluoroalkyl olefins include branched fluorobutenes, such as 1,3,4,4,4-pentafluoro-3-trifluoromethyl) but-1-ene (HFO-1438ezy). In some aspects, there is disclosed a method for dehydrobrominating 4-bromo-1,1,1,2,4-pentafluoro-2-(trifluoromethyl)butane to produce 1,3,4,4,4-pentafluoro-3-(trifluoromethyl)but-1-ene (HFO-1438ezy).
Opening claim text (preview).
What is claimed is: 1. A process comprising the step of contacting 2-bromoheptafluoropropane with vinyl fluoride in the presence of a catalyst, wherein said catalyst is selected from the group consisting of iron, copper and the chloride and bromide salts thereof. 2. The process of claim 1 , wherein the catalyst further comprises a ligand, selected from the group consisting of trialkyl phosphate, triphenyl phosphine, and 2,2-Bipyridyl. 3. The process of claim 2 , wherein the trialkyl phosphate is tributyl phosphate. 4. The process of claim 1 , wherein there is at least from 0.01 moles to 0.1 moles of catalyst per mole of 2-bromoheptafluoropropane. 5. The process of claim 2 , wherein thee is at least from 0.0001 to 0.01 moles of ligand per mole of 2-bromoheptafluoropropane. 6. The process of claim 1 , wherein the molar ratio of vinyl fluoride to 2-bromopropane is from 8:1 to 1:8. 7. The process of claim 1 , wherein the 2-bromoheptafluoropropane is contacted with vinyl fluoride in the presence of catalyst at a temperature of from 75 C. to 300 C. 8. The process of claim 1 , wherein the 2-bromoheptafluoropropane is contacted with vinyl fluoride in the presence of catalyst at a temperature of from 125 C. to 175 C.
by splitting-off hydrogen halides from halogenated hydrocarbons · CPC title
by distillation · CPC title
and bromine · CPC title
of only halogenated hydrocarbons · CPC title
having two carbon atoms · CPC title
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