Boron trifluoride etherate → Methyl 3-fluoro-2-methylbenzoate

HRID 2365731Notes

Reaction equation

HRID 2365731 reaction equation
[F:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].B(F)(F)F.[CH3:16]COCC>CO>[CH3:16][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[C:3]=1[CH3:11]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 2466823-Fluoro-2-methylbenzoic acid

Product 1

HCID 21752566Methyl 3-fluoro-2-methylbenzoateYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-fluoro-2-methyl-benzoic acid (Aldrich, 10.2 g, 66.17 mmol) in methanol (135 mL) at room temperature was treated with boron trifluoride etherate (15 mL) and was allowed to stir at room temperature. The reaction mixture was then concentrated in vacuo to remove the methanol and then diethyl ether (−300 mL) was added. The solution was transferred to a separatory funnel and washed with water (200 mL) and a 5% aqueous sodium bicarbonate solution to pH>7.5. The organic layer was then dried over magnesium sulfate and concentrated in vacuo to afford 3-fluoro-2-methyl-benzoic acid methyl ester (9.74 g, 87%) as a light orange colored oil which was used without purification.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customto remove the methanol
  3. additiondiethyl ether (−300 mL) was added
  4. customThe solution was transferred to a separatory funnel
  5. washwashed with water (200 mL)
  6. dry with materialThe organic layer was then dried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-401291ac9df1416e84974949fea9cbcf
Source dataset
uspto-grants-2014_04
Patent number
US08697705B2

Reaction notes

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