Methanol → 5-Bromo-3-fluoro-2-nitroanisole

HRID 1880966Notes

Reaction equation

HRID 1880966 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](F)[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1.[OH-:13].[K+].[CH3:15]O>>[Br:1][C:2]1[CH:3]=[C:4]([O:13][CH3:15])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 213354875-Bromo-1,3-difluoro-2-nitrobenzene

Product 1

HCID 579556485-Bromo-3-fluoro-2-nitroanisoleYield 63%

Conditions

Temperature
90 °C

Procedure

To a solution of 5-bromo-1,3-difluoro-2-nitrobenzene (2.7 g, 11.3 mmol) in methanol (20 mL) was added potassium hydroxide (680 mg, 12 mmol). The reaction mixture was refluxed at 90° C. for 1 h. It was then concentrated, diluted to ethyl acetate and washed by water and brine. The mixture was then purified by flash column to give the product as red oil (1.8 g, 63%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.94 (s, 3 H) 7.01 (s, 1 H) 7.04 (d, J=8 Hz, 1 H).

Workup

  1. concentrationIt was then concentrated
  2. additiondiluted to ethyl acetate
  3. washwashed by water and brine
  4. customThe mixture was then purified by flash column

Sources & evidence

ORD record
ord-4ecd0678cc8e456bba1e06c721706bf6
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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