Azobisisobutyronitrile → (3-Bromomethyl-phenyl)-acetic acid methyl ester

HRID 480285Notes

Reaction equation

HRID 480285 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1.[Br:13]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.C([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][Br:13])[CH:6]=1

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 5135288Methyl 2-(m-tolyl)acetate

Product 1

HCID 10014651(3-Bromomethyl-phenyl)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of m-tolyl-acetic acid methyl ester (11.41 g, 69.49 mmol), N-bromosuccinimide (12.59 g, 70.73 mmol), AIBN (100 mg) in CCl4 (200 mL) was heated at reflux for 16 h. The reaction was cooled to room temperature and aqueous NaHCO3 (satd) was added. The aqueous solution was extracted with CH2Cl2 (2×) and the organic solution was dried (MgSO4), filtered, and concentrated. Purification by flash chromatography (hexanes to 9:1 hexanes:EtOAc) provided the title compound as a clear and colorless liquid (11.99 g). 1H NMR (CDCl3 400 MHz) δ 7.27 (m, 4H), 4.47 (s, 2H), 3.69 (s, 3H), 3.62 (s, 2H).

Workup

  1. temperatureat reflux for 16 h
  2. extractionThe aqueous solution was extracted with CH2Cl2 (2×)
  3. dry with materialthe organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (hexanes to 9:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-0d94a5052cb24317b3cefcb5ef69cea8
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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