Trimethylamine → 2H-Perfluoro(2-methylpentane)

HRID 1656843Notes

Reaction equation

HRID 1656843 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](O)([CH:8]([F:16])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[C:4]([F:7])([F:6])[F:5].[F:20]C(F)(F)C(F)=C(F)F.CN(C)C.F>O1CCCC1>[F:1][C:2]([F:19])([F:18])[CH:3]([C:8]([F:20])([F:16])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[C:4]([F:7])([F:6])[F:5]

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 8302HexafluoropropyleneHCID 14917Hydrofluoric AcidHCID 19788873HCID 19788873, compound

Product 1

HCID 109141792H-Perfluoro(2-methylpentane)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To prepare 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol, commercially available hexafluoropropene may be oligomerized with commercially available trimethylamine in a dipolar aprotic solvent such as commercially available tetrahydrofuran to provide (CF3)2C:CFCF2CF3 which is then reacted with commercially available hydrogen fluoride to yield 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane as taught by W. Brunskill et al., "Anionic Oligomerisation of Hexafluoropropene: Fission of a Carbon-Carbon Bond by Fluoride Ion", Chemical Communications, 1444 (1970). The 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol.

Workup

  1. customto provide (CF3)2C

Sources & evidence

ORD record
ord-107e8443d2b34600ae9aef851b978bd9
Source dataset
uspto-grants-1993_10
Patent number
US05254755

Reaction notes

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