Water → HCID 68686547, compound

HRID 1994122Notes

Reaction equation

HRID 1994122 reaction equation
[Cl:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[C:4]([OH:11])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.[C:16](=O)([O-])[O-].[Cs+].[Cs+].IC.O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:16])[C:3]=1[C:12]([F:13])([F:14])[F:15]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 68686317HCID 68686317, compound

Product 1

HCID 68686547HCID 68686547, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-chloro-6-nitro-2-(trifluoromethyl)phenol (1.00 g, 4.14 mmol), cesium carbonate (4.05 g, 12.4 mmol), and iodomethane (465 μL, 7.45 mmol) in DMF (20 mL) was allowed to stir at rt overnight. The reaction mixture was diluted with EtOAc and poured into water. The mixture was extracted 3 times with EtOAc and the organic solution was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (SiO2, EtOAc in hexanes) provided the title compound. 1H NMR (300 MHz, CDCl3) δ: 7.90 (d, 1H), 7.40 (d, 1H), and 3.97 (s, 3H).

Workup

  1. extractionThe mixture was extracted 3 times with EtOAc
  2. dry with materialthe organic solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (SiO2, EtOAc in hexanes)

Sources & evidence

ORD record
ord-d9d699c14d9a41a782c1647cd55257b5
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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