Trifluoromethanesulfonic acid → 5-Bromo-2-chloro-4-hydroxybenzonitrile

HRID 576319

Reaction equation

HRID 576319 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(S(O)(=O)=O)(F)(F)F.C1C(=O)N([Br:26])C(=O)C1>CC#N>[Br:26][C:7]1[C:8]([OH:10])=[CH:9][C:2]([Cl:1])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 67184N-bromobutanimideHCID 5927972-Chloro-4-hydroxybenzonitrile

Product 1

HCID 533304525-Bromo-2-chloro-4-hydroxybenzonitrileYield 69.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-4-hydroxybenzonitrile (10 g, 65.1 mmol) in CH3CN (200 mL) was added CF3SO3H (6.33 g, 71.6 mmol) and NBS (16.2 g, 94.1 mmol) at −30° C. After being stirred for 18 hours at room temperature, the mixture was quenched with aq. saturated NaHSO4 solution and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 37 (10.5 g, 66%) as a white solid.

Workup

  1. customthe mixture was quenched with aq. saturated NaHSO4 solution
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f9f150884fbd4cf7a5c01ec1c780055b
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Linked notes

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