Ethyl Acetate → 1-(4-Amino-3-fluoro-phenoxy)-cyclopropanecarboxylic acid methyl ester

HRID 1161348Notes

Reaction equation

HRID 1161348 reaction equation
[CH3:1][O:2][C:3]([C:5]1([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([F:18])[CH:10]=2)[CH2:7][CH2:6]1)=[O:4].C(OCC)(=O)C>C(O)C>[CH3:1][O:2][C:3]([C:5]1([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([F:18])[CH:10]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 671310221-(3-Fluoro-4-nitro-phenoxy)-cyclopropanecarboxylic acid methyl ester

Product 1

HCID 671311211-(4-Amino-3-fluoro-phenoxy)-cyclopropanecarboxylic acid methyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4.49 g (17.6 mmol) 1-(3-fluoro-4-nitro-phenoxy)-cyclopropanecarboxylic acid methyl ester in 50 mL ethanol 0.5 g 10% palladium on charcoal was added and the suspension stirred for 8 h at room temperature under an atmosphere of hydrogen (1.7 bar). After the addition of 100 mL ethyl acetate the catalyst was filtered off, the filtrate evaporated and dried under high vacuum to give the title compound as a brown oil (98%) which was used in the next step without further purification.

Workup

  1. filtrationwas filtered off
  2. customthe filtrate evaporated
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-06deba6810f64f2dab2f8d8be964fa30
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

Loading…