2-Methyl-2-[2-(4-nitro-phenoxy)-phenoxy]-propionic acid tert-butyl ester → 2-[2-(4-Amino-phenoxy)-phenoxy]-2-methyl-propionic acid tert-butyl ester

HRID 1796616Notes

Reaction equation

HRID 1796616 reaction equation
[C:1]([O:5][C:6](=[O:27])[C:7]([CH3:26])([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:27])[C:7]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][C:17]1[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=1)([CH3:26])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 210251752-Methyl-2-[2-(4-nitro-phenoxy)-phenoxy]-propionic acid tert-butyl ester

Product 1

HCID 210251742-[2-(4-Amino-phenoxy)-phenoxy]-2-methyl-propionic acid tert-butyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 388B (1.20 g, 3.21 mmol), 10% Pd/C (360 mg) in MeOH (30 ml) was stirred vigorously under a balloon of H2 for 1.5 h, then filtered through celite and through 0.45μ syringe filter. The filtrate was concentrated to afford 388C (1.08 g, 98%) as a faintly reddish oil. LCMS Found: (M−tBu+2H)+=287.9.

Workup

  1. filtrationfiltered through celite and through 0.45μ syringe
  2. filtrationfilter
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3e83b1717c4a44c89cfdac11690ee0af
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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