Bromine → 4-(Bromomethyl)phenylboronic acid

HRID 273673

Reaktionsgleichung

Reaktionsgleichung von HRID 273673
[Br:1]Br.[B:3]([OH:12])([OH:11])[C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[CH:8][CH:9]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([B:3]([OH:12])[OH:11])=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 24408Bromine3×HCID 79799Tolylboronic acid

Produkt 1

HCID 27355934-(Bromomethyl)phenylboronic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel2×

Versuchsvorschrift

5 mL of bromine solution (2.4 g, 1.5×10-2 mole) in 20 mL of carbon tetrachloride was added to a solution of p-tolylboronic acid (2.0 g, 1.47×10-2 mole) in 40 mL of carbon tetrachloride. The reaction was initiated by illumination with a 150 Watt light bulb. The bromine color faded in 5 minutes and the remaining bromine solution was added over 15 minutes. A solid product precipitated during bromine addition. The solid was filtered and crystallized from chloroform. Yield 1.5 g (49%), m.p. 154°-156° C., 1HNMR (DMSO) δ4.18(s,2H,--CH2Br); 7.37 and 7.74(d,4H,--ArH).

Aufarbeitung

  1. customA solid product precipitated during bromine addition
  2. filtrationThe solid was filtered
  3. customcrystallized from chloroform

Quellen und Nachweise

ORD-Eintrag
ord-b1fbe3cdcef747729d052852c596db56
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387409

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