Sodium Carbonate → HCID 59518017, compound

HRID 1160800Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14](OB(C=C)OCCCC)[CH2:15]CC.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O>[N+:11]([C:3]1[CH:4]=[C:5]([C:8](=[O:10])[CH3:9])[CH:6]=[CH:7][C:2]=1[CH:14]=[CH2:15])([O-:13])=[O:12]

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 4′-bromo-3′-nitroacetophenone (600 mg, 2.46 mmol), vinylboronic acid dibutyl ester (680 mg, 3.69 mmol), and sodium carbonate (1.83 g, 17.22 mmol) in THF/H2O (12 mL/4 mL) is added dichlorobis(triphenylphospine) palladium (II) (86 mg, 5% mmol). The reaction tube is sealed and the mixture is purged with N2 for 3 min and heated at 70° C. for 1.5 h. Then the mixture is cooled to room temperature and poured into saturated ammonia chloride aqueous solution. The mixture is extracted with ethyl acetate (3×20 mL). The organic extracts are combined, washed with brine and concentrated. The crude product is purified with silica gel column chromatography (20% ethyl acetate in hexanes) to afford 1-(3-Nitro-4-vinyl-phenyl)-ethanone as a yellow solid, 87% yield: ESMS m/z 192.0 (M+H+).

Workup

customThe reaction tube is sealed
customthe mixture is purged with N2 for 3 min
temperatureThen the mixture is cooled to room temperature
additionpoured into saturated ammonia chloride aqueous solution
extractionThe mixture is extracted with ethyl acetate (3×20 mL)
washwashed with brine
concentrationconcentrated
customThe crude product is purified with silica gel column chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-ad659d6b225748cc87d5d2efb2a73bd6
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816542B2

Reaction notes

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