Sulfuric Acid → 1035263-42-3

HRID 1868945Notes

Reaction equation

HRID 1868945 reaction equation
[Cl:1][C:2]1[C:3]([I:11])=[C:4](CC#N)[CH:5]=[CH:6][CH:7]=1.[OH:12]S(O)(=O)=O.[O:17]1[CH2:22][CH2:21]OCC1>O>[Cl:1][C:2]1[C:3]([I:11])=[C:4]([CH2:21][C:22]([OH:17])=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 670996963-Chloro-2-iodobenzeneacetonitrile

Product 1

HCID 670999481035263-42-3

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 2-(3-chloro-2-iodophenyl)acetonitrile (3.2 g, 12 mmol) in 20 mL dioxane was treated with 25 mL 9M H2SO4. The mixture was stirred at 115° C. for 2 hours, cooled to room temperature, and diluted with 100 mL water. The mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with saturated NaCl (20 mL), dried over anhydrous sodium sulfate, and concentrated to give crude product in 4 g as pale yellow solid. MS m/e: (M+H)+ 297.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with saturated NaCl (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give crude product in 4 g as pale yellow solid

Sources & evidence

ORD record
ord-1544609d59fb4427a3dad36eea40f324
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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