2-Cyclopropylmethanesulfonyl-4-(2,6-dichloro-4-nitro-phenoxy)-phenol → 4-(4-Amino-2,6-dichloro-phenoxy)-2-cyclopropylmethanesulfonyl-phenol

HRID 584030Notes

Reaction equation

HRID 584030 reaction equation
[CH:1]1([CH2:4][S:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[C:20]([Cl:21])=[CH:19][C:18]([N+:22]([O-])=O)=[CH:17][C:16]=3[Cl:25])[CH:11]=[CH:10][C:9]=2[OH:26])(=[O:7])=[O:6])[CH2:3][CH2:2]1>C(O)C.[Pd]>[NH2:22][C:18]1[CH:17]=[C:16]([Cl:25])[C:15]([O:14][C:12]2[CH:11]=[CH:10][C:9]([OH:26])=[C:8]([S:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)(=[O:7])=[O:6])[CH:13]=2)=[C:20]([Cl:21])[CH:19]=1

Participants

4

Reactant 1

HCID 692587352-Cyclopropylmethanesulfonyl-4-(2,6-dichloro-4-nitro-phenoxy)-phenol

Product 1

HCID 692599874-(4-Amino-2,6-dichloro-phenoxy)-2-cyclopropylmethanesulfonyl-phenolYield 61.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-cyclopropylmethanesulfonyl-4-(2,6-dichloro-4-nitro-phenoxy)-phenol (76 mg, 0.18 mmol) in ethanol (2 mL) was added catalyst 10% Pd/C (27 mg). The mixture was hydrogenated under 45 psi at RT for 12 h. The mixture was filtered through Celite and concentrated to give the title compound of Step E (43 mg) as a solid. The title product of Step E was used in the next step without further purification. MS (APCl−) Calc.: 387.0. Found: 386.2 (M−1).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4c14b804a9df433885a55ffcbfcd5c25
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

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