Cyanuric chloride → 3-Bromo-6-fluoro-2-methoxybenzonitrile

HRID 2175853Notes

Reaction equation

HRID 2175853 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([C:8]([F:11])=[CH:9][CH:10]=1)[C:5]([NH2:7])=O.ClC1N=C(Cl)N=C(Cl)N=1>CN(C=O)C>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([C:8]([F:11])=[CH:9][CH:10]=1)[C:5]#[N:7]

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 71270695HCID 71270695, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromo-6-fluoro-2-methoxybenzamide (14 g, 61 mmol) in 100 mL of DMF was added 2,4,6-trichloro-[1,3,5]triazine (12.3 g, 67.0 mmol) portionwise at 0° C. and stirred for 2 hours before poured to ice/water. The white solid was collected by filtration and was washed with water, dissolved in DCM, dried over anhydrous Na2SO4 and concentrated to afford 3-bromo-6-fluoro-2-methoxybenzonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 7.71˜7.74 (m, 1H), 6.84˜6.88 (m, 1H), 4.09 (s, 3H);

Workup

  1. filtrationThe white solid was collected by filtration
  2. washwas washed with water
  3. dissolutiondissolved in DCM
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-54de9abbc8814c4895429f167ebf3761
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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