Acetic Acid → Methyl 4-bromo-2,6-difluorobenzoate

HRID 595945Notes

Reaction equation

HRID 595945 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:12])[CH:3]=1.[CH3:13][Si](C=[N+]=[N-])(C)C.CC(O)=O>CO>[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([C:6]([O:8][CH3:13])=[O:7])=[C:9]([F:11])[CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 27732984-Bromo-2,6-difluorobenzoic acid

Product 1

HCID 26343953Methyl 4-bromo-2,6-difluorobenzoateYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo-2,6-difluorobenzoic acid (800 mg, 3.38 mmol) in MeOH (11 mL) at room temperature, trimethylsilyldiazomethane (5.63 mL, 3.38 mmol) was slowly added until yellow solution was turned on. The small amount of AcOH was added until yellow color disappered. All volatile materials were removed in vacuo yielding methyl 4-bromo-2,6-difluorobenzoate (47%). LCMS (m/z): 251.1 (MH+), 0.86 min.

Workup

  1. customAll volatile materials were removed in vacuo

Sources & evidence

ORD record
ord-5bb0810bb675496892a635137c9c90a6
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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