Isopropyl iodide → 6-Bromo-2,4'-difluoro-3-isopropoxybiphenyl-4-carbaldehyde

HRID 531099Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

2-Iodopropane (21.7 g) was added to a mixture of 6-bromo-2,4′-difluoro-3-hydroxybiphenyl-4-carbaldehyde (26.7 g) and potassium carbonate (23.6 g) in DMF (250 mL) at room temperature. The mixture was stirred at 60° C. under nitrogen atmosphere for 3 hours. The mixture was quenched with water at room temperature and extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography (hexane/ethyl acetate) to give the title compound (28.5 g).

Workup

customThe mixture was quenched with water at room temperature
extractionextracted with ethyl acetate
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-f1f481d3eb07405299979371ee533462
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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