2-Bromo-3,4-difluoro-1-nitrobenzene → HCID 66751543, compound

HRID 1962880Notes

Reaction equation

HRID 1962880 reaction equation
[CH3:1][O-:2].[Na+].[Br:4][C:5]1[C:10]([F:11])=[C:9](F)[CH:8]=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14]>CS(C)=O>[Br:4][C:5]1[C:10]([F:11])=[C:9]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 5745892-Bromo-3,4-difluoro-1-nitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 66751543HCID 66751543, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

NaOMe (9.5 g) was added portion wise to a solution of 2-bromo-3,4-difluoro-1-nitro-benzene (21.0 g) dissolved in DMSO (250 ml) at room temperature under nitrogen atmosphere. The mixture was stirred for 3 hrs and then poured onto water and extracted with ethyl acetate. The organic phase was extracted with water and brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude product, 2-bromo-3-fluoro-4-methoxy-1-nitro-benzene was used as such in Step 2 described below. 1H NMR (CDCl3) δ ppm: 7.85 (1H, dd); 6.99 (1H, dd); 3.99 (3H, s).

Workup

  1. additionpoured onto water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic phase was extracted with water and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b742a7fc23ff493eb1986406ae538a3e
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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