Water → Methyl 3-bromo-5-nitrobenzoate

HRID 2208749

Reaction equation

HRID 2208749 reaction equation
[Br:1][C:2]1[C:3](C)=[C:4]([N+:12]([O-:14])=[O:13])[C:5](C)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:16](=O)([O-])[O-].[Na+].[Na+].CI.O>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:6]([CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1)[C:7]([O:9][CH3:16])=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 86623945Methyl 5-bromo-2-methyl-3-nitrobenzoic acid

Product 1

HCID 239341Methyl 3-bromo-5-nitrobenzoateYield 104.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To stirred solution of 5-bromo-2,4-dimethyl-3-nitrobenzoic acid (13 g, 47.44 mmol) in DMF (120 mL), sodium carbonate (15 g, 142.2 mmol) and methyl iodide (4.4 ml, 71.16 mmol) were added. Resulting reaction mass was heated at 60° C. for 8 h. On completion, water was added to the reaction mass and extraction was carried out using ethyl acetate. Combined organic layers were washed with sat. bicarbonate solution and 5 N HCl, dried over sodium sulphate, concentrated under reduced pressure giving desired compound (12.9 g, 86%).

Workup

  1. additionwere added
  2. customResulting
  3. customreaction mass
  4. washCombined organic layers were washed with sat. bicarbonate solution and 5 N HCl
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf978c14db984630b8147a13eb9148b8
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Linked notes

Loading…