(1-Bromo-3,6-difluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester → (3,6-Difluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester

HRID 238620Notes

Reaction equation

HRID 238620 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[C:14]([F:15])=[C:13]([OH:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=2)[C:6]=1Br>CO.[Pd]>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[C:14]([F:15])=[C:13]([OH:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=2)[CH:6]=1

Participants

4

Reactant 1

HCID 59326533(1-Bromo-3,6-difluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 59326617(3,6-Difluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl esterYield 65.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (1-bromo-3,6-difluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (50 mg, 0.152 mmol) in methanol was added 10% palladium on carbon (10 mg). After being stirred at room temperature under a hydrogen atmosphere overnight, the resulting mixture was filtered. The filtrate was concentrated in vacuo to afford (3,6-difluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (25 mg, 65%) as a white solid.

Workup

  1. filtrationthe resulting mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ea4dd9d7db304f4187186e33b77771d0
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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