N-bromobutanimide → 3-Bromo-6-methoxy-2-methylbenzonitrile

HRID 1466071Notes

Reaction equation

HRID 1466071 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:4]=1[C:5]#[N:6].C1C(=O)N([Br:19])C(=O)C1>C(O)(C(F)(F)F)=O>[Br:19][C:8]1[C:7]([CH3:11])=[C:4]([C:3]([O:2][CH3:1])=[CH:10][CH:9]=1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5902262-Methoxy-6-methylbenzonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2-methoxy-6-methylbenzonitrile (3.6 g, 24 mmol) in TFA (25 mL) was added NBS (6.5 g, 36 mmol) and stirred at room temperature for 2 hours. Analysis of the reaction mixture by LC indicated complete bromination of the starting material. The solution was concentrated in vacuo and the resulting crude was dissolved in EtOAc and washed with brine, then dried with Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (Hexanes:EtOAc=1:1) to provide the title product.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe resulting crude was dissolved in EtOAc
  3. washwashed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by silica gel column chromatography (Hexanes:EtOAc=1:1)

Sources & evidence

ORD record
ord-a4500d7aca514351bc5fd04744869cbf
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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