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

HRID 1678636Notes

Reaction equation

HRID 1678636 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. MS (TS) m/e (M+H)+: 226.1.

Workup

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

Sources & evidence

ORD record
ord-0ddb22df20ed454caaf462603a0c9ccf
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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