5-Benzyloxy-3'-fluoro-biphenyl-3-carboxylic Acid tert-butyl Ester → 3'-Fluoro-5-hydroxy-biphenyl-3-carboxylic Acid tert-butyl Ester

HRID 1670083Notes

Reaction equation

HRID 1670083 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)[CH:11]=[C:12]([O:14]CC2C=CC=CC=2)[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)[CH:11]=[C:12]([OH:14])[CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 673383235-Benzyloxy-3'-fluoro-biphenyl-3-carboxylic Acid tert-butyl Ester

Product 1

HCID 673398843'-Fluoro-5-hydroxy-biphenyl-3-carboxylic Acid tert-butyl EsterYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Benzyloxy-3′-fluoro-biphenyl-3-carboxylic acid tert-butyl ester (4.1 g) was dissolved in EtOH (50 mL) and hydrogenated in Parr apparatus over 10% Pd/C (410 mg) for 1 h. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to yield the title compound (3.0 g, 96% yield).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8a041e67498849819270c8d9ff68770c
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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