Iodoethane → HCID 18680137, compound

HRID 1633883Notes

Reaction equation

HRID 1633883 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.S([O-])(O)(=O)=O.I[CH2:17][CH3:18].[OH-].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:17][CH3:18])[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 36023(3-Bromophenyl)acetonitrileHCID 61778Sulfate, hydrogen

Product 1

HCID 18680137HCID 18680137, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromophenylacetonitrile (8.12 g) in dichloromethane (150 mL) at room temperature was treated sequentially with tetrabutylammonuim hydrogen sulfate (14.1 g), iodoethane (10 mL), and 15% NaOH (35 mL), stirred for 4 hours, and separated. The aqueous phase was extracted with dichloromethane, and the combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% dichloromethanehexanes to provide the desired product.

Workup

  1. customseparated
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. washthe combined extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 50% dichloromethanehexanes

Sources & evidence

ORD record
ord-57a51a49680f49ecb40a27f7884dc1ee
Source dataset
uspto-grants-2003_01
Patent number
US06504031B1

Reaction notes

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