1-(Cyanomethyl)-3,5-dimethoxybenzene → 1-Bromo-2,4-dimethoxy-6-cyanobenzene

HRID 1060482Notes

Reaction equation

HRID 1060482 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:6]#[N:7].[Br-:13].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Br:13][C:4]1[C:5]([C:6]#[N:7])=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 294821-(Cyanomethyl)-3,5-dimethoxybenzeneHCID 21124087Pyridiniumtribromide

Product 1

HCID 225718291-Bromo-2,4-dimethoxy-6-cyanobenzeneYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-dimethoxybenzonitrile (2 g) in CH2Cl2 (100 mL) was added pyridinium tribromide (4 g). The mixture was stirred for 24 h at room temperature then washed successively with aqueous NaHCO3, water and brine, dried (MgSO4) filtered and evaporated. The residue was crystallized from CH2Cl2 and hexane to yield the title compound (1.8 g).

Workup

  1. washthen washed successively with aqueous NaHCO3, water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was crystallized from CH2Cl2 and hexane

Sources & evidence

ORD record
ord-bcd1791ad2a745d49c91c714a4fa223a
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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