Dimethylformamide → 5-Bromo-2,3-difluoro-4-(trimethylsilyl)benzaldehyde

HRID 34021

Reaction equation

C(NC(C)C)(C)C.[Br:8][C:9]1[C:14]([Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:13]([F:19])[C:12]([F:20])=[CH:11][CH:10]=1.CN(C)[CH:23]=[O:24]>O1CCCC1.CCCCCC.O.C(OCC)(=O)C>[Br:8][C:9]1[C:14]([Si:15]([CH3:16])([CH3:17])[CH3:18])=[C:13]([F:19])[C:12]([F:20])=[C:11]([CH:10]=1)[CH:23]=[O:24]

Participants

Conditions

Temperature: -78 °C

Procedure

Under nitrogen atmosphere, to a solution containing 6.34 mL of N,N-diisopropylamine in 100 mL of tetrahydrofuran, 26.4 mL of 1.57 Mn-butyllithium in hexane was added at 0° C., and stirred at this temperature for 10 minutes. After cooling to −78° C., a solution containing 10.0 g of (6-bromo-2,3-difluorophenyl)trimethylsilane in 100 mL of tetrahydrofuran was added dropwise, stirred at this temperature for 1 hour, then added dropwise with 2.92 mL of N,N-dimethylformamide, allowed to gradually warm to room temperature, and stirred fro 3 hours. After diluting with water and ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (n-hexane), to afford 9.70 g of the title compound as a colorless oil.

Workup

additionwas added at 0° C.
additionwas added dropwise
stirringstirred at this temperature for 1 hour
temperatureto gradually warm to room temperature
stirringstirred fro 3 hours
washthe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated
customThe crude product was purified
customseparated by silica gel column chromatography (n-hexane)

Sources & evidence

ORD record: ord-ffc56b65863d460a9838b0858a75ec3d
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429609B2

Linked notes

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