Methanol → HCID 89649518, compound

HRID 530266Notes

Reaction equation

HRID 530266 reaction equation
[F:1][C:2]([F:22])([O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([N+:16]([O-])=O)=[CH:11][C:10]=1[N+:19]([O-])=O)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4].CO.C1CCCCC1.CCOC(C)=O>C1(C)C=CC=CC=1.[Pd]>[F:22][C:2]([F:1])([O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([NH2:16])=[CH:11][C:10]=1[NH2:19])[C:3]([N:5]([CH3:7])[CH3:6])=[O:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 21867204Cyclohexane ethylacetateHCID 89649225HCID 89649225, compound

Product 1

HCID 89649518HCID 89649518, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2,2-difluoro-2-(2,4-dinitro-5-fluoro-phenoxy)-N,N-dimethyl-acetamide (22.0 g, 68.1 mmol) in toluene (200 g) was added and Pd/C (10% Pd, dry catalyst, 0.7 g, 0.7 mmol). Thereafter, MeOH (80 g) was added and the mixture stirred under an atmosphere of hydrogen (pressure of 0.1 bar) at 45° C. for 90 min. After completion of the reaction the pressure was released, the catalyst was filtered off and the filtrate was evaporated to dryness. The product (17.3 g, 84% pure by NMR, 55.2 mmol, 81% yield) was obtained as an off-white solid. If desired, the purity can be increased by chromatography (SiO2, cyclohexane/EtOAc mixtures).

Workup

  1. customAfter completion of the reaction the pressure
  2. filtrationthe catalyst was filtered off
  3. customthe filtrate was evaporated to dryness
  4. customThe product (17.3 g, 84% pure by NMR, 55.2 mmol, 81% yield) was obtained as an off-white solid

Sources & evidence

ORD record
ord-276df9a8514d4945a23e06afde7598b7
Source dataset
uspto-grants-2016_05
Patent number
US09353070B2

Reaction notes

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