Methyl iodide → 1-Bromo-5-fluoro-4-methoxy-2-nitrobenzene

HRID 639010Notes

Reaction equation

HRID 639010 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([OH:11])=[C:4]([F:12])[CH:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:13][O:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([Br:1])=[CH:3][C:4]=1[F:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 179763164-Bromo-2-fluoro-5-nitrophenol

Product 1

HCID 179763101-Bromo-5-fluoro-4-methoxy-2-nitrobenzeneYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-2-fluoro-5-nitrophenol (25 g, 106 mmol) in DMF (200 mL) was treated with potassium carbonate (28.9 g, 212 mmol) and methyl iodide (12.8 mL, 212 mmol). The reaction mixture was stirred at 60 C for 5 hours and evaporated in vacuo. The mixture was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate and evaporated under vacuum to afford the product (25.6 g, 97%) as a yellow solid. LC-MS (ES) (M+H)+ m/z=251.

Workup

  1. customevaporated in vacuo
  2. customThe mixture was partitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-0a3df1d3f7944ced89caa6387a12a789
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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