Methanol → Methyl 2-bromo-4-fluorobenzoate

HRID 1689766Notes

Reaction equation

HRID 1689766 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([Br:15])[CH:7]=1.[CH3:16]O>>[CH3:16][O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:6]([F:5])=[CH:7][C:8]=1[Br:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 12681692-Bromo-4-fluorobenzoic acid

Product 1

HCID 7210837Methyl 2-bromo-4-fluorobenzoateYield 37%

Procedure

To a solution of thionyl chloride (2.6 mL, 35.7 mmol) in methanol (500 mL) at 0° C. is added 4-fluoro-2-bromo benzoic acid (5.18 g, 23.6 mmol). The mixture is heated to reflux for 19 h. The mixture is concentrated and purified via flash chromatography on silica (120 g) using a gradient of 0 to 80% ethyl acetate in heptane to provide the title compound (2.06 g, 37%) as an oil. MS m/z 233.0 (M+1)

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 19 h
  3. concentrationThe mixture is concentrated
  4. custompurified via flash chromatography on silica (120 g)

Sources & evidence

ORD record
ord-6eebe081622c4549b48dbce442190c09
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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