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

HRID 2042915Notes

Reaction equation

HRID 2042915 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].OS(C(F)(F)F)(=O)=O.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 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-4-hydroxybenzonitrile 11 (10.0 g, 65.1 mmol) in CH3CN (200 mL) were added triflic acid (10 mL, 71.6 mmol), NBS (16.2 g, 91.2 mmol) at −30° C. The mixture was warmed-up to room temperature and stirred at room temperature for 15 h. The reaction was quenched by addition of aq. saturated NaHSO3 solution. The mixture was extracted with EtOAc. The combined organic extract was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography to provide the titled compound 12 (9.8 g, 65%).

Workup

  1. customThe reaction was quenched by addition of aq. saturated NaHSO3 solution
  2. extractionThe mixture was extracted with EtOAc
  3. extractionThe combined organic extract
  4. dry with materialwas dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-47494576a4044d23b1a1c0766eea874b
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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