Bromine → 5-Bromo-2-methoxybenzonitrile

HRID 657334

Reaction equation

HRID 657334 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 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-91481a9d681b44488b6800dcaf7e00da
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Linked notes

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