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

HRID 1502018Notes

Reaction equation

HRID 1502018 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[C:4]#[N:5].C1C(=O)N([Br:19])C(=O)C1>OS(C(F)(F)F)(=O)=O>[Br:19][C:7]1[C:6]([O:10][CH3:11])=[C:3]([C:2]([F:1])=[CH:9][CH:8]=1)[C:4]#[N:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5231012-Fluoro-6-methoxybenzonitrile

Product 1

HCID 712707103-Bromo-6-fluoro-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

2-Fluoro-6-methoxybenzonitrile (8.30 g, 54.9 mmol) was dissolved in Triflic acid (75 mL) at 0° C. then NBS (10.3 g, 57.7 mmol) was added. The reaction mixture was stirred at RT for 1 h. LC-MS showed no starting material peak. The reaction mixture was poured into ice and extracted twice with DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and evaporated to dryness. The residue was purified by chromatography through a 330 g Redi-Sep column and eluted with 10% to 50% EtOAc/hexane solvent system to yield the title compound.

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted twice with DCM
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by chromatography through a 330 g Redi-Sep column
  8. washeluted with 10% to 50% EtOAc/hexane solvent system

Sources & evidence

ORD record
ord-48780755fb014aa7ab36b02c03620474
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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