Water → HCID 23136323, compound

HRID 1678574Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([F:13])[C:5]([O:9][CH2:10][O:11][CH3:12])=[C:6]([F:8])[CH:7]=1.[CH2:14]([O:16][CH:17]([O:20]CC)[CH:18]=[CH2:19])[CH3:15].C(N(C(C)C)CC)(C)C.O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:8][C:6]1[CH:7]=[C:2]([CH2:19][CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:20])[CH:3]=[C:4]([F:13])[C:5]=1[O:9][CH2:10][O:11][CH3:12]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 5-bromo-1,3-difluoro-2-(methoxymethoxy)benzene (4.4 g, 21 mmol), acrolein diethyl acetal (9.4 mL, 62 mmol), tetrabutylammonium chloride (5.7 g, 21 mmol) and diisopropylethylamine (18 mL, 0.10 mol) in N,N-dimethylformamide (40 mL) was added palladium acetate (0.14 g, 0.62 mmol), and the mixture was stirred under argon atmosphere at 90° C. for 18 hours. After the reaction solution was returned to room temperature, water was added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was washed with water, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=49:1 to 4:1) to give the title compound (2.4 g, yield 42%).

Workup

customwas returned to room temperature
extractionthe reaction mixture was extracted with ethyl acetate
washThe extract was washed with water
concentrationconcentrated under reduced pressure
customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=49:1 to 4:1)

Sources & evidence

ORD record: ord-50171cdf40ff4f138d26cea46505dca3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008525B2

Reaction notes

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