Methanol → 5-Bromo-2-nitroanisole

HRID 419459Notes

Reaction equation

HRID 419459 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[CH3:12][O-:13].[Na+].CO>C(Cl)Cl>[CH3:12][O:13][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 27833624-Bromo-2-fluoro-1-nitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 117464905-Bromo-2-nitroanisoleYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To 4-bromo-2-fluoro-1-nitrobenzene (8.0 g, 36.4 mmol) was added 0.5 N sodium methoxide (105 mL, 52.5 mmol). The mixture was stirred at 60° C. for 1 h. The MeOH was rotovaped down. The crude product was dissolved in DCM (100 mL), washed with H2O, dried (Na2SO4), filtered, and rotovaped down to give the title compound of step A (8.1 g, 34.9 mmol, 96%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.74 (d, J=8.61 Hz, 1H), 7.23 (d, J=2.01 Hz, 1H), 7.16 (dd, J=8.61, 1.83 Hz, 1H), 3.95 (s, 3H).

Workup

  1. washwashed with H2O
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-1a0ce796056341a4a6843a20cfa6b0bc
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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