Water → 4-(Bromomethyl)phenylboronic acid

HRID 487415Notes

Reaction equation

HRID 487415 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1.O.[Br:12]Br>CC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:12][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 24408Bromine2×HCID 79799Tolylboronic acid

Product 1

HCID 27355934-(Bromomethyl)phenylboronic acidYield 67.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 62781,1,1-TrichloroethaneSolvent2×

Procedure

A mixture of 4-methylphenylboronic acid (27.2 g; 0.2 mole) in methyl chloroform (250 ml) was heated at reflux with azeotropic removal of water until approximately 2.5 ml of water was collected and a crystalline slurry was formed. A solution of azo(bisisobutyronitrile) (1.0 g) and bromine (32 g) in methyl chloroform (25 ml) was added to the refluxing slurry over 2-3 hours. The mixture was then refluxed until the bromine colour was discharged. The reaction mixture was allowed to cool and stirred at 10°-15° C. for 30 minutes. The suspended solid was collected by filtration, washed with methyl chloroform (2×50 ml) and dried at ambient temperature to give the anhydride of 4-bromomethylphenylboronic acid (29 g) (Compound F) as a white, crystalline solid, which was used without further purification or characterisation.

Workup

  1. temperaturewas heated
  2. customwas collected
  3. customa crystalline slurry was formed
  4. temperatureto cool
  5. filtrationThe suspended solid was collected by filtration
  6. washwashed with methyl chloroform (2×50 ml)
  7. customdried at ambient temperature

Sources & evidence

ORD record
ord-e5c6960ebb18489199080ee358817510
Source dataset
uspto-grants-1994_03
Patent number
US05294716

Reaction notes

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