Water → Methyl 3-bromo-5-methoxybenzoate

HRID 1771669Notes

Reaction equation

HRID 1771669 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9](O)[CH:10]=1)[C:5]([OH:7])=[O:6].[C:12]([O-])([O-])=O.[Cs+].[Cs+].CI.O.CN([CH:24]=[O:25])C>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:25][CH3:24])[CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 157355113-Bromo-5-hydroxybenzoic acid

Product 1

HCID 15618226Methyl 3-bromo-5-methoxybenzoateYield 88%

Procedure

A mixture of 3-bromo-5-hydroxy-benzoic acid (3 g, 13.8 mmol, 1.0 eq) and Cs2CO3 (13.5 g, 41.5 mmol, 3.0 eq) in DMF (60 mL) was stirred at room temperature for 1 h. Methyl iodide (4.9 g, 34.6 mmol, 2.5 eq) was added and the reaction was stirred at room temperature overnight. The resulting mixture was poured into water and extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a colourless oil (3 g, 88%).

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-c8cfb49555b64ae7b1767c06c9aa16d6
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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