m-Tolylacetic acid → 2-(3-(Bromomethyl)phenyl)acetic acid

HRID 990908Notes

Reaction equation

HRID 990908 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Br:12]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:12][CH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 12121m-Tolylacetic acidHCID 67184N-bromobutanimide

Product 1

HCID 103765092-(3-(Bromomethyl)phenyl)acetic acidYield 31%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 3-methylphenylacetic acid (125 g) in tetrachloro methane (1660 ml), N-bromosuccinimide (148 g) and 2,2′-azobisisobutyronitrile (AIBN; 1.37 g) were added. The mixture was refluxed with heating. After termination of reaction, the solution was cooled with ice. The white precipitate was filtered by glass-filter. The filtrate was washed by tetrachloro methane. The filtrate together with washing liquid was concentrated. The obtained residue was dissolved into ethyl acetate. Thereto, hexane was added. The mixture was crystallized to obtain the title compound (59 g).

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating
  3. customAfter termination of reaction
  4. temperaturethe solution was cooled with ice
  5. filtrationThe white precipitate was filtered
  6. filtrationby glass-filter
  7. washThe filtrate was washed by tetrachloro methane
  8. washThe filtrate together with washing liquid
  9. concentrationwas concentrated
  10. dissolutionThe obtained residue was dissolved into ethyl acetate
  11. additionThereto, hexane was added
  12. customThe mixture was crystallized

Sources & evidence

ORD record
ord-48e55850629f48fba4cc1d5c56cfd73b
Source dataset
uspto-grants-2002_10
Patent number
US06462081B1

Reaction notes

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