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

HRID 2175810Notes

Reaction equation

HRID 2175810 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].C1C(=O)N([Br:18])C(=O)C1>OS(C(F)(F)F)(=O)=O>[Br:18][C:7]1[C:6]([CH3:10])=[C:3]([C:2]([F:1])=[CH:9][CH:8]=1)[C:4]#[N:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 186771512-Fluoro-6-methylbenzonitrile

Product 1

HCID 666438523-Bromo-6-fluoro-2-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

Commercially available 2-fluoro-6-methylbenzonitrile (Apollo Scientific, 15.0 g, 111 mmol) was dissolved in triflic acid (75 mL) at 0° C. then NBS (20.7 g, 117 mmol) was added. The reaction mixture was stirred at RT for 1 h then poured into ice water and extracted twice with DCM. The organic layer was washed with brine, dried over Na2SO4, then filtered and evaporated to dryness to yield 3-bromo-6-fluoro-2-methylbenzonitrile: LC-MS: M+1=214, 216.

Workup

  1. extractionextracted twice with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-e7993b85f6834986b6be28a2cabbc71f
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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