1-tert-Butyl-2-(2-nitrophenoxy)benzene → HCID 5104180, compound

HRID 555411Notes

Reaction equation

HRID 555411 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>CO.C1COCC1.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 154152661-tert-Butyl-2-(2-nitrophenoxy)benzene

Product 1

HCID 5104180HCID 5104180, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 1-tert-butyl-2-(2-nitrophenoxy)benzene (20 g, crude) in MeOH/THF (1:1, 200 mL) was added 10% Pd/C (2 g). The mixture was hydrogenated under 75 psi overnight. The mixture was filtered through Celite® cake and the filtrate was evaporated to give the crude product as a black oil. Purification by flash chromatography (0-30% EtOAc/hexane) provided 135a (11 g) as a brown solid.

Workup

  1. customwas hydrogenated under 75 psi overnight
  2. filtrationThe mixture was filtered through Celite® cake
  3. customthe filtrate was evaporated
  4. customto give the crude product as a black oil
  5. customPurification by flash chromatography (0-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-43bcb8774f734ba79eda3e08397005f3
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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