Ethanol → N-methyl-4-[3-(perfluoro-n-octyl)phenoxy]but-2-enamine

HRID 50522Notes

Reaction equation

HRID 50522 reaction equation
Br[CH2:2][CH:3]=[CH:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:37])([F:36])[C:14]([F:35])([F:34])[C:15]([F:33])([F:32])[C:16]([F:31])([F:30])[C:17]([F:29])([F:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])[CH:8]=1.[CH3:38][NH2:39].C(O)C>O1CCCC1>[CH3:38][NH:39][CH2:2][CH:3]=[CH:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:37])([F:36])[C:14]([F:35])([F:34])[C:15]([F:33])([F:32])[C:16]([F:31])([F:30])[C:17]([F:29])([F:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])[CH:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 865836481-Bromo-4-[3-(perfluoro-n-octyl)phenoxy]but-2-ene

Product 1

HCID 86583649N-methyl-4-[3-(perfluoro-n-octyl)phenoxy]but-2-enamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (1-bromo-4-[3-(perfluoro-n-octyl)phenoxy]but-2-ene (12.9 g) in tetrahydrofuran (20 mL) is added to a solution of 40 wt % methyl amine (20 mL), ethanol (20 mL) and tetrahydrofuran (20 mL) at 40° C. The mixture is stirred at ambient temperature for 2 hr. and extracted in the normal fashion. The resulting oil is Kugelrohr distilled to give N-methyl-4-[3-(perfluoro-n-octyl)phenoxy]but-2-enamine.

Workup

  1. extractionand extracted in the normal fashion
  2. distillationdistilled

Sources & evidence

ORD record
ord-fbdeb0bdc3494eb5842babe351eae9a0
Source dataset
uspto-grants-2004_03
Patent number
US06713135B2

Reaction notes

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