Methyl iodide → HCID 66859027, compound

HRID 1803152Notes

Reaction equation

HRID 1803152 reaction equation
[H-].[Na+].[F:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:5]=1[OH:14].I[CH3:16]>CN(C=O)C.C1COCC1>[F:10][C:9]1[CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=[C:5]([O:14][CH3:16])[C:4]=1[F:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 221546562,3-Difluoro-5-nitrophenol

Product 1

HCID 66859027HCID 66859027, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Step M (4): Sodium hydride (120 mg, 5 mmol) was added to a solution of 2,3-difluoro-5-nitrophenol (250 mg, 1.4 mmol) in DMF/THF (4 mL/4 mL). After 10 min, iodomethane (0.2 mL, 5 mmol) was added. The mixture was heated at 80° C. for 2 h. The reaction mixture was quenched with 1 N HCl. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford 1,2-difluoro-3-methoxy-5-nitrobenzene (130 mg, 48% yield).

Workup

  1. customThe reaction mixture was quenched with 1 N HCl
  2. additionThe mixture was diluted with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-114c7bea4d444778843b552a07b23c9c
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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