[6-Chloro-4-(4-methanesulfonyl-phenoxy)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester → [4-(4-Methanesulfonyl-phenoxy)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

HRID 238613

Reaction equation

HRID 238613 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10](Cl)[CH:11]=2)[CH:6]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:21][CH:22]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1

Participants

4

Reactant 1

HCID 59326613[6-Chloro-4-(4-methanesulfonyl-phenoxy)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

Product 1

HCID 59326489[4-(4-Methanesulfonyl-phenoxy)-3-methyl-naphthalen-2-yl]-acetic acid methyl esterYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [6-chloro-4-(4-methanesulfonyl-phenoxy)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (110 mg, 0.26 mmol) in methanol (3 mL) was added 10% palladium on carbon (10 mg). The resulting mixture was vigorously stirred at room temperature overnight under a hydrogen atmosphere (balloon) and then filtered. The filtrate was concentrated in vacuo to give [4-(4-methanesulfonyl-phenoxy)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (68 mg, 67%) as a colorless oil which was directly used in the next step without further purification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-932d0f3023c341b399c673e0a2378596
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Linked notes

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