Carbon tetrabromide → 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-bromoethyl)phenyl]butanamide

HRID 35025

Reaktionsgleichung

Reaktionsgleichung von HRID 35025
[F:1][C:2]([F:22])([C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13]O)=[CH:8][CH:7]=1)=[O:4].C(Br)(Br)(Br)[Br:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.P>O1CCCC1.C(OCC)C>[F:1][C:2]([F:22])([C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][Br:24])=[CH:8][CH:7]=1)=[O:4]

Komponenten

7

Edukt 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 24404PhosphineHCID 212977062,2,3,3,4,4,4-heptafluoro-N-[4-(2-hydroxyethyl)phenyl]butanamide

Produkt 1

HCID 212977022,2,3,3,4,4,4-heptafluoro-N-[4-(2-bromoethyl)phenyl]butanamideAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-hydroxyethyl)phenyl]butanamide (25 g), carbon tetrabromide (51 g), diethyl ether (140 mL) and tetrahydrofuran (140 mL) was cooled in ice and treated with triphenylphosphine (39.3 g), portionwise. When addition of the phosphine was complete, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The precipitate was removed by filtration and the filtrate concentrated in vacuo. The residue was purified by chromatography on silica gel, eluted with dichloromethane to give 16.2 g of 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-bromoethyl)phenyl]butanamide as a white solid.

Aufarbeitung

  1. temperaturewas cooled in ice
  2. customThe precipitate was removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel
  5. washeluted with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-4dd549727dfd4ba6bb0cc01ce71d4299
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04764623

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