Bromine → 5-Bromo-2-methoxybenzonitrile

HRID 564455

Reaction equation

HRID 564455 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8]>C(Cl)(Cl)Cl>[Br:1][C:10]1[CH:11]=[CH:12][C:5]([O:4][CH3:3])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

4

Reactant 2

HCID 24408BromineHCID 810862-Methoxybenzonitrile

Product 1

HCID 44185605-Bromo-2-methoxybenzonitrileYield 71.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Bromine (13.7 g, 86.0 mmol) in CHCl3 (20 mL) was added to the solution of 2-(methyloxy)benzonitrile (10.9 g, 81.9 mmol) in CHCl3 (50 mL). The mixture was refluxed for 29 h. The reaction was allowed to cool to room temperature, and washed with saturated sodium bisulfite (50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 5-bromo-2-(methyloxy)benzonitrile (12.4 g, 71%).

Workup

  1. temperatureThe mixture was refluxed for 29 h
  2. washwashed with saturated sodium bisulfite (50 mL), and brine (50 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-14736655450840e29eadb95eeb1761f1
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Linked notes

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