Water → 2,3-Difluoro-4'-(11-bromoundecyl)oxybiphenyl

HRID 1289377

Reaktionsgleichung

Reaktionsgleichung von HRID 1289377
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]O)=[CH:11][CH:10]=1.O.P(Br)(Br)[Br:30]>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][Br:30])=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 189208442,3-Difluoro-4'-(11-hydroxyundecyl)oxybiphenyl

Produkt 1

HCID 189208562,3-Difluoro-4'-(11-bromoundecyl)oxybiphenylAusbeute 120,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel2×

Versuchsvorschrift

First, 8 g of 2,3-difluoro-4'-(11-hydroxyundecyl)oxybiphenyl and 100 ml of carbon tetrachloride were placed in a 200 ml flask. A solution in which 2.3 g of phosphorus tribromide was dissolved in 50 ml of carbon tetrachloride was added dropwise to the reaction mixture under ice water cooling, and the resultant reaction mixture was stirred at room temperature for 3 hours and under reflux for 2 hours. The reaction mixture was poured into water, and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/9) and recrystallized from hexane to obtain 4.5 g of 2,3-difluoro-4'-(11-bromoundecyl)oxybiphenyl (Y: 47.8%). The compound thus obtained had a purity of 95.3% by GC.

Aufarbeitung

  1. additionwas added dropwise to the reaction mixture under ice water cooling
  2. customthe resultant reaction mixture
  3. temperatureunder reflux for 2 hours
  4. extractionan organic layer was extracted with ether
  5. washThe ether layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThereafter, the solvent was distilled away
  8. customThe residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/9)
  9. customrecrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-c96f040139dd4a30bda7577dba9eae5c
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750213

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