Dimethylformamide → 4-Chloro-1-fluoro-2-methoxybenzene

HRID 591452Notes

Reaction equation

HRID 591452 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.[CH3:10]N(C=O)C.C([O-])([O-])=O.[K+].[K+].IC>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([O:8][CH3:10])[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 224828215-Chloro-2-fluorophenol

Product 1

HCID 178217034-Chloro-1-fluoro-2-methoxybenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5-chloro-2-fluorophenol (4.68 g) and DMF (dry) (50 mL) were added K2CO3 (8.83 g) and iodomethane (3.99 mL) at room temperature. The mixture was stirred at room temperature for 4.5 h. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed successively with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (4.60 g).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed successively with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-c17a3d49cd7b4003a169b8a0cec99d4e
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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