Hydrochloric Acid → HCID 826099, compound

HRID 1397261Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Br:14])[CH:13]=1)[C:7]([O:9]C)=[O:8])(=O)[CH3:2].[OH-].[K+].O.NN.Cl>C(O)CO.O>[Br:14][C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([CH2:1][CH3:2])[CH:13]=1)[C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 200 °C

Procedure

The compound methyl 3-acetyl-5-bromobenzoate (1.2 g, 4.8 mmol) was dissolved in ethylene glycol (10 mL) and KOH (0.41 g, 7.3 mmol) followed by hydrazine hydrate (0.44 mL, 7.3 mmol) were added. The reaction mixture was heated to 200° C. for 1 h. The reaction mixture was cooled to room temperature and diluted with water. The pH of the aqueous layer was adjusted to 2-3 using 1.5N HCl. 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 50% EtOAc in petroleum ether) to yield 3-bromo-5-ethylbenzoic acid (0.95 g, yield 89%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.07 (m, 1H), 7.88 (m, 1H), 7.59 (m, 1H), 2.73 (q, J=7.6 Hz, 2H), 1.28 (t, J=7.6 Hz, 3H). MS (ESI) m/z: Calculated for C9H9BrO2: 227.98. found: 229.0 (M+H)+.

Workup

additionwere added
temperatureThe reaction mixture was cooled to room temperature
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 50% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-80d501bb7e0f4435a6fd65a586a09251
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901156B2

Reaction notes

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