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

HRID 890740Notes

Reaction equation

HRID 890740 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 aqueuos 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-2060ba87d3ba4e5b9e740b6b76bfa784
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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