N-bromobutanimide → 5-Bromo-4-fluoro-2-methoxy-benzonitrile

HRID 2175843Notes

Reaction equation

HRID 2175843 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1.C1C(=O)N([Br:19])C(=O)C1>OS(O)(=O)=O>[Br:19][C:9]1[C:2]([F:1])=[CH:3][C:4]([O:10][CH3:11])=[C:5]([CH:8]=1)[C:6]#[N:7]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27833294-Fluoro-2-methoxybenzonitrile

Product 1

HCID 712707665-Bromo-4-fluoro-2-methoxy-benzonitrile

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 4-fluoro-2-methoxybenzonitrile (35 g, 0.23 mol) in 300 mL of concentrated H2SO4 was added NBS (42 g, 0.23 mol) portionwise at −10° C. and the reaction was stirred at r.t. for 2 hours. Then the reaction was poured into 2 L of ice portionwise, and the solid precipitated out was filtered. The filter cake was washed with water, then the solid was dried in vacuo to give 5-bromo-4-fluoro-2-methoxybenzonitrile.

Workup

  1. customthe solid precipitated out
  2. filtrationwas filtered
  3. washThe filter cake was washed with water
  4. customthe solid was dried in vacuo

Sources & evidence

ORD record
ord-87379817a12d40e1ac3f0ccc499f3235
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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