(2-Cyclopropyl-2',4'-difluoro-5-isopropoxybiphenyl-4-yl)methanol → 2-Cyclopropyl-2',4'-difluoro-5-isopropoxybiphenyl-4-carbaldehyde

HRID 2272489Notes

Reaction equation

HRID 2272489 reaction equation
[CH:1]1([C:4]2[CH:9]=[C:8]([CH2:10][OH:11])[C:7]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:6][C:5]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH2:3][CH2:2]1>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH:1]1([C:4]2[CH:9]=[C:8]([CH:10]=[O:11])[C:7]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:6][C:5]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 117992205(2-Cyclopropyl-2',4'-difluoro-5-isopropoxybiphenyl-4-yl)methanol

Product 1

HCID 1179922452-Cyclopropyl-2',4'-difluoro-5-isopropoxybiphenyl-4-carbaldehydeYield 89.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

Manganese dioxide (10.8 g) was added to a toluene (30 mL) solution of (2-cyclopropyl-2′,4′-difluoro-5-isopropoxybiphenyl-4-yl)methanol (3.97 g), and the mixture was stirred at 60 C for 1 hour in a nitrogen atmosphere. The reaction mixture was filtered, and then, 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 (3.53 g).

Workup

  1. filtrationThe reaction mixture was filtered
  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-6de7f2d18d7946a0b583023af9524f94
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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