Azobisisobutyronitrile → Methyl 3'-(bromomethyl)-4-chlorobiphenyl-3-carboxylate

HRID 404953Notes

Reaction equation

HRID 404953 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)=[CH:4][C:3]=1[C:15]([O:17][CH3:18])=[O:16].C1C(=O)N([Br:26])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:26][CH2:14][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:15]([O:17][CH3:18])=[O:16])[CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 66799518Methyl 4-chloro-3'-methylbiphenyl-3-carboxylate

Product 1

HCID 50994825Methyl 3'-(bromomethyl)-4-chlorobiphenyl-3-carboxylateYield 95.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 4-chloro-3′-methylbiphenyl-3-carboxylate (1.77 g, 6.5 mmol) and NBS (1.27 g, 7.19 mmol) were dissolved in CCl4 (20 mL), a catalytic amount of AIBN was added and the mixture was heated at reflux overnight. The reaction mixture was filtered, the solvent was removed in vacuo and the residue was purified using automated medium pressure silica gel chromatography (ISCO) eluting with 20% ethyl acetate/hexane to obtain methyl 3′-(bromo-methyl)-4-chlorobiphenyl-3-carboxylate (2.10 g, 91%) as a pale brown solid. 1H NMR (300 MHz, CDCl3): δ 8.07 (s, 1H), 7.68-7.45 (m, 6H), 4.58 (s, 2H), 4.00 (s, 3H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent was removed in vacuo
  5. customthe residue was purified
  6. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c72e13bdef4843139370cec25eded228
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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