Bromine → 4-(Bromomethyl)phenylboronic acid

HRID 2081162Notes

Reaction equation

HRID 2081162 reaction equation
[B:1]([OH:10])([OH:9])[C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[Br:11]Br>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([B:1]([OH:10])[OH:9])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 24408Bromine4×HCID 79799Tolylboronic acid

Product 1

HCID 27355934-(Bromomethyl)phenylboronic acid

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

Into a solution of p-tolylboronic acid (2.0 g, 1.47×10-2 mol) in 40 ml of carbon tetrachloride was added 5 ml of a bromine solution prepared by dissolving 2.4 g of bromine (1.5×10-2 mol) in 20 ml of CCl4. The reaction was initiated by illumination with a 150 watt light bulb. The bromine color faded in 5 minutes. The remaining bromine solution was added after 15 minutes. The precipitate that formed was isolated by filtration, and recrystallized from chloroform. M.P. 154°-156° C.

Workup

  1. customprepared
  2. customThe precipitate that formed
  3. customwas isolated by filtration
  4. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-67a4dc6084bb4d298fd949001e15cd79
Source dataset
uspto-grants-1993_02
Patent number
US05183653

Reaction notes

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