1,2-Dimethoxyethane → 1-Bromo-3-(perfluoro-tert-butyl)propane

HRID 1456878

Reaction equation

HRID 1456878 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=[C:8]([F:10])[F:9])[C:4]([F:7])([F:6])[F:5].[F-:13].[Cs+].Br[C:16]([Br:19])(C)C.[CH2:20]([CH2:23]OC)OC>>[Br:19][CH2:16][CH2:20][CH2:23][C:3]([C:8]([F:13])([F:9])[F:10])([C:4]([F:7])([F:6])[F:5])[C:2]([F:11])([F:12])[F:1]

Participants

5

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 116582,2-DibromopropaneHCID 25953Cesium fluorideHCID 611091,1,3,3,3-Pentafluoro-2-(trifluoromethyl)-1-propene

Product 1

HCID 542553231-Bromo-3-(perfluoro-tert-butyl)propane

Procedure

Compound (19) is prepared by a method analogous to the one described by Shinkai et al. (1990, supra). Compound (3) is converted to the sodium salt with excess sodium hydride in a solvent such as tetrahydrofuran or dimethylformamide and then reacted 1-bromo-3-(perfluoro-tert-butyl)propane to furnish Compound (19) which is purified by crystallization or chromatography. 1-bromo-3-(perfluoro-tert-butyl)propane is prepared by reacting perfluoroisobutylene and cesium fluoride in a solvent like monoglyme with excess dibromopropane as described by Rogers et al. (1993, U.S. Pat. No. 5,234,680).

Workup

  1. customis purified by crystallization or chromatography

Sources & evidence

ORD record
ord-0827a6b3bbc246b9aa23ace1b80091a6
Source dataset
uspto-grants-1998_12
Patent number
US05846515

Linked notes

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