Methyl 5-fluoro-2-(2-nitrophenoxy)benzoate → Methyl 2-(2-aminophenoxy)-5-fluorobenzoate

HRID 1946571Notes

Reaction equation

HRID 1946571 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]>C(O)C.C(O)(=O)C.C1COCC1.[Pd]>[NH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 1

HCID 59783776Methyl 5-fluoro-2-(2-nitrophenoxy)benzoate

Product 1

HCID 59783706Methyl 2-(2-aminophenoxy)-5-fluorobenzoateYield 95%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of title compound 18 (3.48 g, 11.9 mmol) in ethanol (30 mL), acetic acid (1.0 mL) and THF (10 mL) was added palladium on charcol 10% (0.37 g, 10% w/w). The reaction mixture was stirred under hydrogen atmosphere for 20 hours. The catalyst was filtered and the filtrate was concentrated in vacuo. The residue was diluted with ether and this organic mixture was washed with a saturated aqueous solution of bicarbonate, water and brine then solvent evaporated to afford title compound 19 (2.95 g, 95%) as a beige solid. LRMS (ESI): (calc) 261.08 (found) 262.3 (MS)+.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was diluted with ether
  4. washthis organic mixture was washed with a saturated aqueous solution of bicarbonate, water and brine
  5. customsolvent evaporated

Sources & evidence

ORD record
ord-2f552711c6744014807b818e11067714
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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