Triphenylphosphine dibromide → 4-Bromo-4'-(bromomethyl)-1,1'-biphenyl

HRID 900359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 900359
[Br: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.[Br:16]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][Br:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 70579Triphenylphosphine dibromideHCID 1393673[4-(4-Bromophenyl)phenyl]methanol

Produkt 1

HCID 201373444-Bromo-4'-(bromomethyl)-1,1'-biphenyl

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (4′-bromo-biphenyl-4-yl)-methanol, 7.01 g (27.9 mmol) and dibromo-triphenylphosphorane 11.8 g (27.9 mmol) in 150 mL of methylene chloride stirred at room temperature for 2 h. The solution was diluted with 100 mL of water and extracted with 2×200 mL portions of diethyl ether. The organic layers were combined, washed with sat. aq. NaCl, and dried (MgSO4). After the solution was concentrated, the residue was purified through a short plug of silica gel (eluted with 50% EtOAc-Heptane) to afford the desired product in 9.1 g (100%) as a white solid. The material was taken to the next step without further purification.

Aufarbeitung

  1. extractionextracted with 2×200 mL portions of diethyl ether
  2. washwashed with sat. aq. NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationAfter the solution was concentrated
  5. customthe residue was purified through a short plug of silica gel (eluted with 50% EtOAc-Heptane)

Quellen und Nachweise

ORD-Eintrag
ord-f24cf759e8084102ba3549a64e16f83a
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07358248B2

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