Methyl iodide → Methyl 2-bromo-6-methoxybenzoate

HRID 1476826Notes

Reaction equation

HRID 1476826 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].[C:13]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 111178812-Bromo-6-methoxybenzoic acid

Product 1

HCID 13940770Methyl 2-bromo-6-methoxybenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-bromo-6-methoxybenzoic acid (40 g, 0.176 mol) in DMF (300 mL) was added K2CO3 (24.8 g, 0.176 mol) and CH3I (37 g, 0.264 mol). The mixture was stirred at RT overnight. The reaction was quenched with 1M HCl aq and the mixture was extracted with EtOAc (3×300 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound (41 g, 99%).

Workup

  1. customThe reaction was quenched with 1M HCl aq
  2. extractionthe mixture was extracted with EtOAc (3×300 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2776bd83b7b14bef9a8a03714cccfc5e
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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