2-(4-Benzyloxy-3,5-difluoro-phenyl)-cyclopropane-carboxylic acid ethyl ester → Ethyl 2-(3,5-difluoro-4-hydroxyphenyl)cyclopropanecarboxylate

HRID 62877Notes

Reaction equation

HRID 62877 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[C:13]([F:15])[C:12]([O:16]CC2C=CC=CC=2)=[C:11]([F:24])[CH:10]=1)=[O:5])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:10]=[C:11]([F:24])[C:12]([OH:16])=[C:13]([F:15])[CH:14]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 594198442-(4-Benzyloxy-3,5-difluoro-phenyl)-cyclopropane-carboxylic acid ethyl ester

Product 1

HCID 59419842Ethyl 2-(3,5-difluoro-4-hydroxyphenyl)cyclopropanecarboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-Benzyloxy-3,5-difluoro-phenyl)-cyclopropane-carboxylic acid ethyl ester (0.65 g, 1.96 mmol) obtained in Step A was dissolved in EtOH (15 mL), and 10% Pd/C (65 mg) was added thereto. The mixture was stirred at room temperature under hydrogen atmosphere for 3 hours. The reactant was filtered by using celite and concentrated under reduced pressure to obtain the title compound (0.46 g, 97%).

Workup

  1. filtrationThe reactant was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-be53fa67ab0e438e8e0b5d5d7c51c900
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

Loading…