HCID 12056886, compound → 3,5-Dichloro-4-[3-[[5-(trifluoromethyl)-2-pyridinyl]oxy]propoxy]phenol

HRID 1420506Notes

Reaction equation

HRID 1420506 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=2)=[C:11]([Cl:31])[CH:10]=1)C1C=CC=CC=1.[H][H]>[C].[Pd].C(OCC)(=O)C>[Cl:31][C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[C:13]([Cl:15])[C:12]=1[O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][N:22]=1

Participants

5

Reactant 2

HCID 12056886HCID 12056886, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 185045573,5-Dichloro-4-[3-[[5-(trifluoromethyl)-2-pyridinyl]oxy]propoxy]phenolYield 92%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A reaction vessel was charged with 0.5 g of 1-benzyloxy-3,5-dichloro-4-(3-(5-trifluoromethylpyridin-2-yloxy)propyloxy)benzene and 50 ml of ethyl acetate, and the air in the vessel was replaced with nitrogen. Then, 0.3 g of 10% palladium carbon was added, and the nitrogen in the vessel was replaced with hydrogen, followed by stirring at room temperature for 24 hours. The hydrogen in the vessel was replaced with nitrogen, after which the reaction mixture was filtered through Celite, and the filtrate was concentrated, which afforded 0.36 g of 3,5-dichloro-4-(3-(5-trifluoromethylpyridin-2-yloxy)propyloxy)phenol (92% yield).

Workup

  1. filtrationafter which the reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e155928f2f4e42359f04acf3adcff140
Source dataset
uspto-grants-2000_06
Patent number
US06071861

Reaction notes

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