Hydrogen Bromide → 4-(Bromomethyl)phenylacetic acid

HRID 47787

Reaction equation

HRID 47787 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[BrH:12].BrBr>ClC(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 248474p-Tolylacetic acid

Product 1

HCID 45190564-(Bromomethyl)phenylacetic acid

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a stirred solution of p-methylphenylacetic acid (0.175 mol, 27.8 g) in tetrachloromethane (250 mL) under a nitrogen atmosphere in a round bottom flask equipped with a reflux condenser and provision for trapping the released HBr was added bromine (0.175 mol, 27.8 g) dissolved in tetrachloromethane. The red/brown mixture was irradiated and brought to reflux with a 250 watt incandescent light source. Over the course of ten minutes, the color was discharged and a crystalline precipitate was formed. The mixture was allowed to cool to room temperature, and the solid was collected by vacuum filtration, and dried in a stream of nitrogen to give (4-bromomethyl-phenyl)-acetic acid as a white solid containing 6.3% by weight p-methylphenylacetic acid as an impurity. (25.1 g, 63%).

Workup

  1. customThe red/brown mixture was irradiated
  2. temperatureto reflux with a 250 watt incandescent light source
  3. customOver the course of ten minutes
  4. customa crystalline precipitate was formed
  5. filtrationthe solid was collected by vacuum filtration
  6. customdried in a stream of nitrogen

Sources & evidence

ORD record
ord-9555f4d9c8914c59af9dc1e2342d6db4
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Linked notes

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