Methyl 5-(benzyloxy)-2-cyclopropyl-2',4'-difluorobiphenyl-4-carboxylate → Methyl 2-cyclopropyl-2',4'-difluoro-5-hydroxybiphenyl-4-carboxylate

HRID 531076Notes

Reaction equation

HRID 531076 reaction equation
C([O:8][C:9]1[C:10]([C:26]([O:28][CH3:29])=[O:27])=[CH:11][C:12]([CH:23]2[CH2:25][CH2:24]2)=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH:14]=1)C1C=CC=CC=1.[H][H]>[C].[Pd].C1COCC1>[CH:23]1([C:12]2[CH:11]=[C:10]([C:26]([O:28][CH3:29])=[O:27])[C:9]([OH:8])=[CH:14][C:13]=2[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 117992146Methyl 5-(benzyloxy)-2-cyclopropyl-2',4'-difluorobiphenyl-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 117992303Methyl 2-cyclopropyl-2',4'-difluoro-5-hydroxybiphenyl-4-carboxylateYield 95.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 5-(benzyloxy)-2-cyclopropyl-2′,4′-difluorobiphenyl-4-carboxylate (20.3 g), 10% palladium carbon (containing 55% water, 10 g), and THF (100 mL) was stirred at room temperature for 1 hour in a hydrogen atmosphere. The catalyst was filtered off, and then, the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (15.0 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9f5335aafc164d5fa978c7b546d639ec
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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