Diazomethane → Methyl 4-bromo-2,3,5,6-tetrafluorobenzoate

HRID 1470616Notes

Reaction equation

HRID 1470616 reaction equation
[Br:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:13])[C:3]=1[F:14].[N+](=[CH2:17])=[N-]>CO>[CH3:17][O:7][C:6](=[O:8])[C:5]1[C:4]([F:13])=[C:3]([F:14])[C:2]([Br:1])=[C:10]([F:11])[C:9]=1[F:12]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 2981734-Bromo-2,3,5,6-tetrafluorobenzoic acid

Product 1

HCID 46311226Methyl 4-bromo-2,3,5,6-tetrafluorobenzoateYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo-2,3,5,6-tetrafluoro-benzoic acid (20 g, 73.49 mmol) in methanol (20 mL) was added an ethereal solution of diazomethane gas until the starting material is completely consumed. Reaction mixture was then evaporated under reduced pressure. The crude solid obtained was purified by flash column chromatography using 5% ethyl acetate in hexane, to obtain title compound as colorless crystalline solid (18 g, 85%).

Workup

  1. customis completely consumed
  2. customReaction mixture
  3. customwas then evaporated under reduced pressure
  4. customThe crude solid obtained
  5. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-d77135383d1b4b8db240f572ea533946
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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