Methanol → Methyl 2-bromo-4-fluorobenzoate

HRID 541483Notes

Reaction equation

HRID 541483 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 12681692-Bromo-4-fluorobenzoic acid

Product 1

HCID 7210837Methyl 2-bromo-4-fluorobenzoateYield 95%

Conditions

Temperature
85 °C

Procedure

Into a round-bottom flask, was placed a solution of 2-bromo-4-fluorobenzoic acid (21.8 g, 99.5 mmol, 1.00 equiv) in a solvent mixture of sulfuric acid (20 mL) and methanol (20 mL). The resulting solution was stirred for 5 h at 85° C., then cooled and cooled and concentrated in vacuo. The residue was diluted with ethyl acetate (200 mL) and washed with brine (200 mL) then aqueous NaHCO3 (100 mL. Note: gas evolution), dried (Na2SO4), filtered and concentrated in vacuo to obtain the title compound as a light yellow oil (22.0 g, 95%).

Workup

  1. customInto a round-bottom flask, was placed
  2. temperaturecooled
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with ethyl acetate (200 mL)
  6. washwashed with brine (200 mL)
  7. dry with materialaqueous NaHCO3 (100 mL. Note: gas evolution), dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-266b60404c2d4ab5abf194d22c294fb3
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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