Carbon Tetrachloride → Methyl 3-bromo-4-(bromomethyl)benzoate

HRID 2261258Notes

Reaction equation

HRID 2261258 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].C(Cl)(Cl)(Cl)Cl.C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][Br:25])[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 7015747Methyl 3-bromo-4-methylbenzoate

Product 1

HCID 10804694Methyl 3-bromo-4-(bromomethyl)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 3-bromo-4-methylbenzoate (6.56 g, 28.64 mmol), carbon tetrachloride (100 mL), NBS (6.07 g, 34.10 mmol) and AIBN (150 mg, 0.91 mmol) were heated at reflux for 18 h. The reaction mixture was cooled and diluted with DCM (200 mL) and water (100 ml) and washed with 5% NaHCO3 saturated solution (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure (rotary evaporator) affording an oily residue.

Workup

  1. temperatureat reflux for 18 h
  2. temperatureThe reaction mixture was cooled
  3. washwashed with 5% NaHCO3 saturated solution (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure (rotary evaporator)
  7. customaffording an oily residue

Sources & evidence

ORD record
ord-4eb07a7f7a1b48caa959ea1bf8edf043
Source dataset
uspto-grants-2010_12
Patent number
US07846944B2

Reaction notes

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