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

HRID 2272482Notes

Reaction equation

HRID 2272482 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, 10.0 g), and THF (100 mL) was stirred at room temperature for 1 hour in a hydrogen atmosphere of balloon pressure. The catalyst was filtered off, and the solvent was distilled off 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. distillationthe solvent was distilled off under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-469c87959fc743b08f3326c422f66478
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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