Dimethyl Sulfate → Methyl 5-bromo-4-fluoro-2-methoxy-3-nitrobenzoate

HRID 17520Notes

Reaction equation

HRID 17520 reaction equation
[Br:1][C:2]1[C:3]([F:15])=[C:4]([N+:12]([O-:14])=[O:13])[C:5](O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:16](=O)([O-])[O-].[K+].[K+].S([O:27][CH3:28])(OC)(=O)=O>C(#N)C>[Br:1][C:2]1[C:3]([F:15])=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([O:27][CH3:28])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:16])=[O:8]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 860974835-Bromo-4-fluoro-2-hydroxy-3-nitrobenzoic Acid

Product 1

HCID 86097486Methyl 5-bromo-4-fluoro-2-methoxy-3-nitrobenzoateYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Bromo-4-fluoro-2-hydroxy-3-nitrobenzoic acid (I-228) (35.89 g, 0.128 mol) was dissolved in acetonitrile (600 ml), then at room temperature, potassium carbonate (53.1 g, 0.358 mol) was added, and dimethyl sulfate (30.3 ml, 0.32 mol was dropwise added. After staring at 60° C. for 2.5 hour and then cooling to room temperature, the insoluble matter was removed by filtration (with washing with acetonitrile (400 ml)). The filtrate was concentrated under reduced pressure (about 800 ml of acetonitrile was evaporated away), and water (800 ml) was added to the residue, followed by stirring at room temperature. The precipitated crystal was washed with water and dried to obtain the entitled compound (36.5 g, 92%) as a pale yellow solid.

Workup

  1. customthe insoluble matter was removed by filtration (with washing with acetonitrile (400 ml))
  2. concentrationThe filtrate was concentrated under reduced pressure (about 800 ml of acetonitrile
  3. customwas evaporated away), and water (800 ml)
  4. additionwas added to the residue
  5. washThe precipitated crystal was washed with water
  6. customdried

Sources & evidence

ORD record
ord-817f578aa2bd495588519a1bd2cabb1e
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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