Bromine → 5-Bromo-2-methoxybenzonitrile

HRID 662036Notes

Reaction equation

HRID 662036 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

Br2 (13.7 g, 86.0 mmol) in CHCl3 (20 mL) was added to a 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-ee9078e3cb3d4d9ca94b6bdff0d821a7
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Reaction notes

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