Methyl iodide → HCID 117599530, compound

HRID 513242Notes

Reaction equation

HRID 513242 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:23])[CH:6]([C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:24]I>CN(C=O)C.[NH4+].[Cl-]>[CH3:3][O:4][C:5](=[O:23])[C:6]([C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21])([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:24]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 117599770HCID 117599770, compound

Product 1

HCID 117599530HCID 117599530, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

NaH (562 mg, 23.4 mmol) is added portion wise to a solution of (5-Bromo-2-nitro-phenyl)-phenyl-acetic acid methyl ester (6.8 g, 19.5 mmol) in DMF (100 mL) at room temperature and stirred at room temperature for 3 hours. MeI (8.3 g, 58.5 mmol) is added to the above mixture at 0° C. The mixture is warmed to room temperature slowly and stirred overnight. The mixture is diluted with saturated aqueous NH4Cl solution and extracted with ethyl acetate (3×100 mL). The combined organic phase is washed with water and brine, dried over Na2SO4, filtered and concentrated to give the product.

Workup

  1. temperatureThe mixture is warmed to room temperature slowly
  2. stirringstirred overnight
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic phase is washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the product

Sources & evidence

ORD record
ord-ff17e2452bda40f98649f053790dc996
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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