Diazomethane → Methyl 4-bromo-2,3,5,6-tetrafluorobenzoate
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
Product 1
Reagents, catalysts & solvents 1
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
- customis completely consumed
- customReaction mixture
- customwas then evaporated under reduced pressure
- customThe crude solid obtained
- 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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