Water → 2-Fluoro-3-methoxy-6-nitrophenol

HRID 2368091Notes

Reaction equation

HRID 2368091 reaction equation
[F:1][C:2]1[C:7]([O:8]C)=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=[CH:4][C:3]=1[O:13][CH3:14].CCCCCC.BrB(Br)Br.O>C1(C)C=CC=CC=1>[F:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 962WaterHCID 104654172-Fluoro-1,3-dimethoxy-4-nitrobenzeneHCID 19780039HCID 19780039, compound

Product 1

HCID 104199412-Fluoro-3-methoxy-6-nitrophenolYield 61.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-fluoro-1,3-dimethoxy-4-nitrobenzene (1.5 g) in toluene (100 mL) was added 1 M tribromoborane hexane solution (16 mL) at 0° C., and the mixture was stirred at room temperature for 15 hr. Water was added to the reaction mixture at 0° C., and the mixture was stirred at room temperature for 10 min. The reaction solution was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (860 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 10 min
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washthe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f415bdf6dd494cba80c31b155918ba4e
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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