Trifluoromethanesulfonic acid → HCID 118497051, compound

HRID 522150Notes

Reaction equation

HRID 522150 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].OS(C(F)(F)F)(=O)=O.[Br:21]N1C(=O)CCC1=O>CC#N>[Br:21][C:9]1[C:10]([OH:12])=[CH:11][C:2]([Cl:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 67184N-bromobutanimideHCID 134988302-Chloro-4-hydroxy-benzoic acid methyl ester

Product 1

HCID 118497051HCID 118497051, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 2-chloro-4-hydroxybenzoate (5.0 g, 26.8 mmol) in MeCN (100 mL) was cooled to −30° C. Triflic acid (2.60 mL, 29.48 mmol) was added followed by N-bromosuccinimide (5.25 g, 29.48 mmol) and the reaction was warmed to room temperature and stirred for 1.5 hours. The reaction was quenched by the addition of saturated aqueous Na2CO3 solution (50 mL). The solution was extracted with EtOAc (2×100 mL), the combined organic layers were combined, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 20-40% EtOAc in heptanes to afford the title compound as a white solid (2.60 g, 37%).

Workup

  1. customThe reaction was quenched by the addition of saturated aqueous Na2CO3 solution (50 mL)
  2. extractionThe solution was extracted with EtOAc (2×100 mL)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with 20-40% EtOAc in heptanes

Sources & evidence

ORD record
ord-1a487335e1d149d6934cc481fab7c867
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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