Water → Methyl 2-bromo-3-nitrobenzoate

HRID 2208779Notes

Reaction equation

HRID 2208779 reaction equation
[Br:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[C:14](=O)([O-])[O-].[Na+].[Na+].CI.O>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 6946292HCID 6946292, compound

Product 1

HCID 79263Methyl 2-bromo-3-nitrobenzoateYield 126.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-bromo-3-nitrobenzoate (3 g, 12.19 mmol) in DMF (33 mL), sodium carbonate (5.16 g, 48.67 mmol) and methyl iodide (6.92 g, 48.67 mmol) were added. Resulting reaction mixture was heated at 60° C. for 4 h. On completion, water was added to the mixture and extraction carried out using DCM. The combined organic layers were dried and concentrated under reduced pressure to obtain crude methyl 2-bromo-3-nitrobenzoate (4 g, crude).

Workup

  1. customResulting
  2. customreaction mixture
  3. customThe combined organic layers were dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e10a6a04cf64c79a6a72e6859bd5892
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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