Triethylamine → Ethyl 3-{3,5-difluoro-2-[2-(ethoxycarbonyl)vinyl]phenyl}acrylate

HRID 863059Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1Br.C(N([CH2:16][CH3:17])CC)C.[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[CH:19]=[CH2:20]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.NN>[F:9][C:4]1[C:3]([CH:20]=[CH:19][C:18]([O:22][CH2:16][CH3:17])=[O:21])=[C:2]([CH:20]=[CH:19][C:18]([O:22][CH2:23][CH3:24])=[O:21])[CH:7]=[C:6]([F:8])[CH:5]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 1,2-dibromo-3,5-difluorobenzene (24.7 g, 91.6 mmol), bis(triphenylphosphine)palladium(II) chloride (2.57 g, 3.66 mmol) and triethylamine (51.0 mL, 366 mmol) in 300 mL of DMF was stirred under argon at approximately 85° C. for 15 minutes. Hydrazine hydrate (366 μL, 7.54 mmol) was added and the mixture was stirred for an additional 10 minutes. Ethyl acrylate (39.7 mL, 366 mmol) was added and the mixture was stirred under argon at approximately 85° C. for approximately 144 hours. The solvents were removed by evaporation under reduced pressure and the residue was dissolved in 1.0 L of ethyl acetate. The ethyl acetate solution was washed 3 times with water and dried over magnesium sulfate. Evaporation of the solvent gave crude ethyl 3-{3,5-difluoro-2-[2-(ethoxycarbonyl)vinyl]phenyl}acrylate (36 g).

Workup

stirringthe mixture was stirred for an additional 10 minutes
stirringthe mixture was stirred under argon at approximately 85° C. for approximately 144 hours
customThe solvents were removed by evaporation under reduced pressure
dissolutionthe residue was dissolved in 1.0 L of ethyl acetate
washThe ethyl acetate solution was washed 3 times with water
dry with materialdried over magnesium sulfate
customEvaporation of the solvent

Sources & evidence

ORD record: ord-a161b7b22f1745aebb6fb90192301cf9
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719280

Reaction notes

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