Phosphorus tribromide → 4-(Bromomethyl)-4'-fluoro-1,1'-biphenyl

HRID 257067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 257067
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.P(Br)(Br)[Br:17]>CCOCC.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][Br:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 24614Phosphorus tribromideHCID 1394497[4-(4-Fluorophenyl)phenyl]methanol

Produkt 1

HCID 189638634-(Bromomethyl)-4'-fluoro-1,1'-biphenyl

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 4'-fluoro-4-biphenylylmethanol (7.38 g, 36.93 mmol) in Et2O (250 ml) is added phosphorous tribromide (7 ml, 73.06 mmol). The reaction is allowed to warm slowly to room temperature and is then refluxed for 12 hours. After the reaction is cooled to room temperature ice chips are added until gas no longer evolves. The reaction mixture is then diluted with H2O (200 ml) and extracted with 1N NaOH (300 ml) and saturated NaCl solution (300 ml), dried over MgSO4, and concentrated in vacuo to give 4'-fluoro-4-biphenylylmethyl bromide as a white solid.

Aufarbeitung

  1. temperatureis then refluxed for 12 hours
  2. temperatureAfter the reaction is cooled to room temperature ice chips
  3. additionare added until gas
  4. extractionextracted with 1N NaOH (300 ml) and saturated NaCl solution (300 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-03fdd78720b94ed59ac2c865bc3ff4c1
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05260316

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