Methyl iodide → HCID 59443044, compound

HRID 2380886Notes

Reaction equation

HRID 2380886 reaction equation
CI.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:11])=[C:6]([OH:19])[CH:5]=1.[C:20](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:11])=[C:6]([O:19][CH3:20])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10060688HCID 10060688, compound

Product 1

HCID 59443044HCID 59443044, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (1.10 mL) was added to a suspension of (4-chloro-2-hydroxyphenyl)(4-fluorophenyl)methanone (3.00 g) and potassium carbonate (3.30 g) in N,N-dimethylformamide (50 mL) and the mixture was stirred at room temperature for 2.5 hours. The reaction solution was filtered through Celite and the filtrate was poured into an aqueous saturated ammonium chloride solution. The mixture was extracted with ethyl acetate and the organic layer was washed successively with water and brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=30/1) to give the titled compound (2.95 g) as a pale yellow powder.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. additionthe filtrate was poured into an aqueous saturated ammonium chloride solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed successively with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=30/1)

Sources & evidence

ORD record
ord-760f4d6db5cf40e796291d47ef7ee832
Source dataset
uspto-grants-2012_09
Patent number
US08258131B2

Reaction notes

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