Bromine → 3-Bromo-6-methoxy-2-methylbenzonitrile

HRID 2173221Notes

Reaction equation

HRID 2173221 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:6]=1[C:7]#[N:8]>C(Cl)(Cl)(Cl)Cl.[Fe]>[Br:1][C:10]1[C:9]([CH3:13])=[C:6]([C:5]([O:4][CH3:3])=[CH:12][CH:11]=1)[C:7]#[N:8]

Participants

5

Reactant 2

HCID 24408BromineHCID 5902262-Methoxy-6-methylbenzonitrile

Product 1

HCID 675160643-Bromo-6-methoxy-2-methylbenzonitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of Br2 (261 mg, 1.63 mmol) in CCl4 (1 mL) was added over 15 min to a solution of 2-methoxy-6-methylbenzonitrile in CCl4 (3 mL) at −10° C. containing 4 mg of Fe powder. After 45 min the reaction was poured into ice water (10 mL). The organic layer was washed with Na2SO3 (aq.) solution (10 mL*2), brine (20 mL) and dried over Na2SO4, concentrated in vacuo to give 3-bromo-6-methoxy-2-methylbenzonitrile.

Workup

  1. washThe organic layer was washed with Na2SO3 (aq.) solution (10 mL*2), brine (20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56803d2b069049ea98f67b2c651480d3
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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