Sodium Methoxide → HCID 17980129, compound

HRID 1666811Notes

Reaction equation

HRID 1666811 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][O-:14].[Na+]>CO>[Br:1][C:2]1[CH:7]=[C:6]([O:14][CH3:13])[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 192615421-Bromo-4,5-difluoro-2-nitrobenzene

Product 1

HCID 17980129HCID 17980129, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 1-bromo-4,5-difluoro-2-nitrobenzene (24 g, 100 mmol) to a solution of sodium methoxide (1.2 eq) in MeOH. After addition, stir the reaction at room temperature for 2.5 hours. Remove the solvent in vacuo and dilute the residue with water and extract with Et2O (2×250 mL). Combine the organic layers, dry over MgSO4, filter, and the remove solvent in vacuo to give 1-bromo-4-fluoro-5-methoxy-2-nitrobenzene as a yellow solid: 1H NMR (300 MHz, CDCl3): 3.99 (s, 3H), 7.26 (m, 1H), 7.83 (d, 1H); MS (ED+): m/z 249, 251 (M+); Analysis for C7H5BrFNO3: Calcd.: C, 33.63; H, 2.02; N, 5.60. found: C, 33.79; H, 1.98; N, 5.62.

Workup

  1. additionAfter addition
  2. customthe reaction at room temperature for 2.5 hours
  3. customRemove the solvent in vacuo
  4. additiondilute the residue with water
  5. extractionextract with Et2O (2×250 mL)
  6. dry with materialCombine the organic layers, dry over MgSO4
  7. filtrationfilter

Sources & evidence

ORD record
ord-ce8c2b4bf23c494b8bba0f6b92926dd8
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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