Ethyl Acetate → 4-(4-Amino-2,6-dimethylphenoxy)-2-(4-fluorobenzenesulfonyl)phenol

HRID 2086166Notes

Reaction equation

HRID 2086166 reaction equation
[CH3:1][C:2]1[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[C:22]([CH3:29])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:6]=1.C(OCC)(=O)C>C(O)C.[Pd]>[NH2:26][C:24]1[CH:23]=[C:22]([CH3:29])[C:3]([O:4][C:5]2[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([S:12]([C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)(=[O:14])=[O:13])[CH:6]=2)=[C:2]([CH3:1])[CH:25]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 223448994-(2,6-Dimethyl-4-nitrophenoxy)-2-(4-fluorobenzenesulfonyl)phenol

Product 1

HCID 223448764-(4-Amino-2,6-dimethylphenoxy)-2-(4-fluorobenzenesulfonyl)phenolYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(2,6-dimethyl-4-nitro-phenoxy)-2-(4-fluoro-benzenesulfonyl)-phenol (11.4 grams, 27.4 mmol) in a mixture of ethanol (200 mL and ethyl acetate (200 mL) was added catalyst (10% palladium on carbon, 2.3 grams). The mixture was hydrogenated under 45 psi at room temperature for 4 hours. The mixture was filtered through Celite and concentrated to give the title compound of Step D (10.5 grams) as a tan solid. The product was used in the next step without further purification. 1H NMR (400 MHz, CD3OD) δ7.98-7.92 (m, 2H), 7.29-7.22 (m, 2H), 7.21 (d, 1H), 6.92 (dd, 1H), 6.78 (d, 1H), 1.98 (s, 6H). MS (APCI−) Calc.:387.1, Found: 386.2 (M−1).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-630ded3b775b43be9b1abe07553e011e
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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