Toluene → Methyl 3-fluoro-4-methylbenzoate

HRID 220768Notes

Reaction equation

HRID 220768 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([OH:11])=[O:10].[C:16]1(C)C=CC=CC=1>>[CH3:16][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([CH3:15])=[C:6]([F:5])[CH:7]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 676873-Fluoro-p-toluic acid

Product 1

HCID 18973767Methyl 3-fluoro-4-methylbenzoateYield 83%

Procedure

Thionyl chloride (9.62 g, 81 mmol) was added to a solution of 3-fluoro-4-methylbenzoic acid (5.0 g, 32.4 mmol) in toluene (50 ml). The mixture was stirred at room temperature for 1.5 h and heated at reflux for 3 h. The sol-vent was removed in vacuo and the residue was taken up in methanol (30 ml) and CH2Cl2 (30 ml) and stirred for 18 h. The mixture was evaporated in vacuo and the residue was taken up in EtOAc (50 ml), washed with saturated NaHCO3 solution (3×75 ml), dried and evaporated in vacuo to yield the title compound (4.5 g, 83%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customThe sol-vent was removed in vacuo
  4. stirringCH2Cl2 (30 ml) and stirred for 18 h
  5. customThe mixture was evaporated in vacuo
  6. washwashed with saturated NaHCO3 solution (3×75 ml)
  7. customdried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a92516418eb34081835e188e8b1ab188
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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