p-Toluenesulfonic acid monohydrate → HCID 89955260, compound

HRID 1526785Notes

Reaction equation

HRID 1526785 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]([CH3:17])([CH3:16])[C:14]#[N:15])[CH:5]=[C:6]([CH:8]2OCC[O:9]2)[CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:13]([CH3:17])([CH3:16])[C:14]#[N:15])[CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 89955627HCID 89955627, compound

Product 1

HCID 89955260HCID 89955260, compoundYield 123.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(3-bromo-5-(1,3-dioxolan-2-yl)phenyl)-2-methylpropanenitrile (1.9836 g, 6.70 mmol) in acetone (25 mL) was added p-toluenesulfonic acid hydrate (0.26 g, 1.36 mmol) and the reaction mixture was stirred at room temperature overnight to give an orange-red solution. The solvent was evaporated in vacuo to give an orange-brown residue. The residue was partitioned between aqueous saturated NaHCO3 solution (25 mL) and ethyl acetate (50 mL), the organic layer was removed, washed with brine (1×25 mL), dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to give an orange viscous liquid (2.08 g). Purification of the crude product by silica-gel flash chromatography on silica gel column and elution with 5-40% ethyl acetate in n-hexane afforded the desired product as a pale yellow crystalline solid (0.89 g). LC-MS analysis of the solid shows the desired product's mass: m/z 252 (79BrM+H), m/z 254 (81BrM+H); Calcd for C11H10BrNO: 252.11

Workup

  1. customto give an orange-red solution
  2. customThe solvent was evaporated in vacuo
  3. customto give an orange-brown residue
  4. customThe residue was partitioned between aqueous saturated NaHCO3 solution (25 mL) and ethyl acetate (50 mL)
  5. customthe organic layer was removed
  6. washwashed with brine (1×25 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-32f0699ee74245dba4afda646cc44c41
Source dataset
uspto-grants-2015_07
Patent number
US09085606B2

Reaction notes

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