(2-Chloro-6-cyclopropyl-2',4'-difluoro-3-methoxybiphenyl-4-yl)methanol → 2-Chloro-6-cyclopropyl-2',4'-difluoro-3-methoxybiphenyl-4-carbaldehyde

HRID 531080Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Manganese dioxide (2.29 g) was added at room temperature to a toluene (30 mL) solution of (2-chloro-6-cyclopropyl-2′,4′-difluoro-3-methoxybiphenyl-4-yl)methanol (1.07 g), and the mixture was stirred at 80° C. for 1 hour in a nitrogen atmosphere. The reaction mixture was filtered through celite, 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 (978 mg).

Workup

filtrationThe reaction mixture was filtered through celite
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-9ef274f0606645fcb977a95f2f357dae
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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