Ethyl Acetate → 4-Bromo-2-fluoro-benzoic acid methyl ester

HRID 2168338Notes

Reaction equation

HRID 2168338 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.[C:12](OCC)(=O)C.C[Si](C=[N+]=[N-])(C)C>CO>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 167693TrimethylsilyldiazomethaneHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 113453114-Bromo-2-fluoro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Bromo-2-fluorobenzoic acid (5.00 g) was added to ethyl acetate (35 mL) and methanol (35 mL). Trimethylsilyldiazomethane (2M solution in diethyl ether, 12.56 mL) was added slowly and the solution was mixed at room temperature for 30 minutes. The solvent was removed under vacuum, and the crude material was dissolved in ethyl acetate. The solution was extracted with 0.5M sodium hydroxide and dried with brine then anhydrous sodium sulfate. After filtration, the solvent was removed under vacuum to afford crude product of sufficient purity for subsequent use.

Workup

  1. additionthe solution was mixed at room temperature for 30 minutes
  2. customThe solvent was removed under vacuum
  3. dissolutionthe crude material was dissolved in ethyl acetate
  4. extractionThe solution was extracted with 0.5M sodium hydroxide
  5. dry with materialdried with brine
  6. filtrationAfter filtration
  7. customthe solvent was removed under vacuum
  8. customto afford crude product of sufficient purity for subsequent use

Sources & evidence

ORD record
ord-4460dccf41d24763969217c0b60a8129
Source dataset
uspto-grants-2015_06
Patent number
US09045420B2

Reaction notes

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