Tetrabutylammonium Fluoride → 2-Bromo-6-fluoro-3,4-dimethoxybenzonitrile

HRID 1582384Notes

Reaction equation

HRID 1582384 reaction equation
[F-:1].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:19][C:20]1[C:27]([O:28][CH3:29])=[C:26]([O:30][CH3:31])[CH:25]=[C:24]([N+]([O-])=O)[C:21]=1[C:22]#[N:23]>C(OCC)(=O)C>[Br:19][C:20]1[C:27]([O:28][CH3:29])=[C:26]([O:30][CH3:31])[CH:25]=[C:24]([F:1])[C:21]=1[C:22]#[N:23]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 227212172-Bromo-3,4-dimethoxy-6-nitrobenzonitrile

Product 1

HCID 227212132-Bromo-6-fluoro-3,4-dimethoxybenzonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A partially dried solution of tetrabutylammonium flouride (24 ml, 1M in THF stored over 4A sieves) was added to 2-bromo-3,4-dimethoxy-6-nitrobenzonitrile (prepared according to step (c), 1.73 g, 6.02 mmol) with stirring at room temperature. After 1 hour ethyl acetate was added and the mixture washed with 1M aqueous HCl (50 ml). The aqueous wash was extracted with ethyl acetate (50 ml) and the combined organics then washed with aqueous NaHCO3 (50 ml) before being dried over MgSO4 and concentrated in vacuo. The crude residue was recrystallised from toluene:tert-butylmethylether (1:1) to give 1.34 g of the subtitle product (85%).

Workup

  1. washthe mixture washed with 1M aqueous HCl (50 ml)
  2. washThe aqueous wash
  3. extractionwas extracted with ethyl acetate (50 ml)
  4. washthe combined organics then washed with aqueous NaHCO3 (50 ml)
  5. dry with materialbefore being dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was recrystallised from toluene:tert-butylmethylether (1:1)

Sources & evidence

ORD record
ord-a90c0015477b4c4eb58cf3c9438a68a4
Source dataset
uspto-grants-2004_05
Patent number
US06734303B2

Reaction notes

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