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

HRID 1470658Notes

Reaction equation

HRID 1470658 reaction equation
[NH2:1][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-]>CCOCC>[CH3:17][O:7][C:6](=[O:8])[C:5]1[C:4]([F:13])=[C:3]([F:14])[C:2]([NH2:1])=[C:10]([F:11])[C:9]=1[F:12]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 703454-Amino-2,3,5,6-tetrafluorobenzoic acid

Product 1

HCID 2782457Methyl 4-amino-2,3,5,6-tetrafluorobenzoateYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-amino-2,3,5,6-tetrafluoro-benzoic acid (1.0 g, 4.78 mmol) in ether (75 mL), an ethereal solution of diazomethane gas was added until the starting material is completely consumed. The reaction mixture was then evaporated under reduced pressure. The crude solid obtained was purified by flash column chromatography using 0.5% ethyl acetate in hexane to obtain title compound (0.8 g, 75%).

Workup

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

Sources & evidence

ORD record
ord-d1f2262dfd0040ffad7eb2d4ac302303
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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