4-(3-Bromo-4-methoxyphenoxy)-3,5-dimethylnitrobenzene → 4-(3-Bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenylamine

HRID 584037Notes

Reaction equation

HRID 584037 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N+:13]([O-])=O)=[CH:8][C:7]=1[CH3:16]>[Pd].C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([NH2:13])=[CH:8][C:7]=1[CH3:16]

Participants

4

Reactant 1

HCID 223397284-(3-Bromo-4-methoxyphenoxy)-3,5-dimethylnitrobenzene

Product 1

HCID 223395024-(3-Bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenylamineYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the title product of Step A (5.0 g) and 10% palladium on carbon (0.6 g) in ethyl acetate (100 ml) was hydrogenated at 50 psi for 3 h. The reaction was filtered through Celite and concentrated to afford the title compound of Step B as a yellow solid (4.3 g). MS (APCl+) Calc: 321; Found 322 (M+1).

Workup

  1. filtrationThe reaction was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-72fd1386b1924835a94407742935102a
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

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