Dimethylformamide → (E)-ethyl 3-(2-amino-5-bromophenyl)acrylate

HRID 1504399Notes

Reaction equation

[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4](I)[CH:3]=1.C(=O)(O)[O-].[Na+].[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH:16]=[CH2:17].CN(C=O)C>O>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1/[CH:17]=[CH:16]/[C:15]([O:19][CH2:20][CH3:21])=[O:18]

Participants

Conditions

Temperature: 80 °C

Procedure

To a microwave vial was added, 4-bromo-2-iodoaniline (1.70 g, 5.71 mmol), PdOAc2 (0.064 g, 0.285 mmol), sodium bicarbonate (1.198 g, 14.27 mmol), ethyl acrylate (0.651 ml, 5.99 mmol) and DMF (1.902 ml). The reaction was heated in microwave for 1 hour at 80° C. The reaction was cooled to room temperature, diluted with water and extracted with DCM (3×). The combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The resulting material was concentrated, dissolved in minimal DCM and purified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane) to afford 0.860 g of (E)-ethyl 3-(2-amino-5-bromophenyl)acrylate. m/z (ESI) 270.1 (M+H)+.

Workup

additionTo a microwave vial was added
temperatureThe reaction was cooled to room temperature
extractionextracted with DCM (3×)
washThe combined organics were washed with water and brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
concentrationThe resulting material was concentrated
dissolutiondissolved in minimal DCM
custompurified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane)

Sources & evidence

ORD record: ord-6ac906ec0f1e438aace2af5e4a584e1b
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212182B2

Reaction notes

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