HCID 86677590, compound → HCID 67323924, compound

HRID 1397260Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12](=[O:17])N(OC)C)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:18][Mg]Cl>C1COCC1>[C:12]([C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([Br:1])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:17])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

The compound methyl 3-bromo-5-(methoxy(methyl)carbamoyl)benzoate (2.3 g, 7.6 mmol) was dissolved in dry THF (50 mL), solution was cooled to 0° C. and methylmagnesium chloride (3M in THF, 2.5 mL, 7.6 mmol)) was added dropwise. The reaction mixture was slowly allowed to come to room temperature and stirred further for 6 h. The reaction mixture was cooled to 0° C. and quenched with saturated NH4Cl solution. The product was extracted with EtOAc. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluent 5% EtOAc in petroleum ether) to get methyl 3-acetyl-5-bromobenzoate (0.95 g, yield 49%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.51 (t, J=1.3 Hz, 1H), 8.37 (t, J=1.7 Hz, 1H), 8.28 (t, J=1.6 Hz, 1H), 3.97 (s, 3H), 2.65 (s, 3H).

Workup

customto come to room temperature
temperatureThe reaction mixture was cooled to 0° C.
customquenched with saturated NH4Cl solution
extractionThe product was extracted with EtOAc
washThe organic layer was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed under reduced pressure
customThe crude product was purified by column chromatography (silica 60-120 mesh, eluent 5% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-2b36207596484506a5cedc1dacfb55c5
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901156B2

Reaction notes

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