2-(4-Benzyloxy-3,5-difluoro-phenyl)-cyclopropane carboxylic acid methyl ester → 2-(3,5-Difluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl ester

HRID 62906Notes

Reaction equation

HRID 62906 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:7][CH:6]1[C:8]1[CH:13]=[C:12]([F:14])[C:11]([O:15]CC2C=CC=CC=2)=[C:10]([F:23])[CH:9]=1)=[O:4]>C1COCC1.CO.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:7][CH:6]1[C:8]1[CH:9]=[C:10]([F:23])[C:11]([OH:15])=[C:12]([F:14])[CH:13]=1)=[O:4]

Participants

4

Reactant 1

HCID 901180272-(4-Benzyloxy-3,5-difluoro-phenyl)-cyclopropane carboxylic acid methyl ester

Product 1

HCID 901181212-(3,5-Difluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid methyl esterYield 112.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-(4-Benzyloxy-3,5-difluoro-phenyl)-cyclopropanecarboxylic acid methyl ester (21 mg, 0.066 mmol) obtained in Step B was dissolved in THF/MeOH (1 mL/1 mL), and Pd/C (10%, 10 mg) was added thereto. The mixture was stirred under hydroten atmosphere for 12 hours, filtered by using celite, and concentrated under reduced pressure to obtain the title compound (17 mg, 99%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a8fddb2f451b44b88387152dc446d294
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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