Carbon Tetrachloride → 4-(Bromomethyl)phenylacetic acid

HRID 1384468Notes

Reaction equation

HRID 1384468 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.[Br:12]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl>O>[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 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 248474p-Tolylacetic acid

Product 1

HCID 45190564-(Bromomethyl)phenylacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50 g (0.33 mol) of 4-methylphenyl acetic acid, 62 g (0.35 mol) of N-bromo-succinimide, 200 ml of carbon tetrachloride and 0.1 g of 2,2-azobis(isobutyronitrile) are placed in a 500 ml flask and heated to reflux with stirring for 4 hours. After the reaction mixture is cooled to room temperature, it is poured into 500 ml of water. The obtained precipitate is filtered off, and then washed with water. After drying under an atmosphere of reduced pressure, 55 g of a white powder are obtained (72%).

Workup

  1. customare placed in a 500 ml flask
  2. temperatureheated
  3. temperatureto reflux
  4. filtrationThe obtained precipitate is filtered off
  5. washwashed with water
  6. dry with materialAfter drying under an atmosphere of reduced pressure, 55 g of a white powder
  7. customare obtained (72%)

Sources & evidence

ORD record
ord-819175ecd056427081e0bb77dca02629
Source dataset
uspto-grants-2001_07
Patent number
US06258954B1

Reaction notes

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