Diethyl Ether → Methyl 3-bromo-4-fluorobenzoate

HRID 2244103Notes

Reaction equation

HRID 2244103 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=[O:6].[Si](C=[N+]=[N-])(C)(C)[CH3:13].CCOCC>C1COCC1.CO>[CH3:13][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([F:11])=[C:2]([Br:1])[CH:3]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 705093-Bromo-4-fluorobenzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 7018022Methyl 3-bromo-4-fluorobenzoateYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-4-fluoro-benzoic acid (2.5 g, 11.42 mmol) was placed in a 100 ml round bottom flask charged with a stir bar, sealed with a septum and placed under a nitrogen atmosphere and dissolved in 9 ml dry THF and 3 ml dry MeOH. A 2.0M solution of TMS diazomethane in ether (6.28 ml, 12.56 mmol) was added dropwise to the stirring solution of the acid. Conversion of the acid to the ester was complete after twenty minutes according to LC/MS analysis. The solvent was removed under reduced pressure and product was used without further purification. Recovered a light oil (2.66 g, 100% yield) LC/MS (10-99%) M/Z 234, retention time 3.09 minutes.

Workup

  1. additioncharged with a stir bar
  2. customsealed with a septum
  3. customThe solvent was removed under reduced pressure and product
  4. customwas used without further purification

Sources & evidence

ORD record
ord-b7dbdf3e6d5f4df386bffcbe68b3432f
Source dataset
uspto-grants-2010_03
Patent number
US07678802B2

Reaction notes

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