Methanol → 1-Bromo-2-fluoro-5-methoxy-4-nitrobenzene

HRID 419448

Reaction equation

HRID 419448 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[F:12].[CH3:13][O-:14].[Na+].CO>C(Cl)Cl>[CH3:13][O:14][C:6]1[CH:7]=[C:2]([Br:1])[C:3]([F:12])=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 27362864-Bromo-2,5-difluoronitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 223473121-Bromo-2-fluoro-5-methoxy-4-nitrobenzeneYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To 1-bromo-2,5-difluoro-4-nitrobenzene (5.0 g, 21 mmol) was added 0.5 N sodium methoxide (50 mL, 25 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 (5 g, 20 mmol, 95%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.69 (s, 1H), 7.28 (s, 1H), 3.95 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-f3a7673b827643669d7dc4972db4a14c
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Linked notes

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