Hydrochloric Acid → Methyl 3-acetyl-5-(methylsulfonyl)benzoic acid

HRID 1454197Notizen

Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:11]=1)[C:5]([O:7]C)=[O:6].[CH:16]([O:18]CCCC)=[CH2:17].[CH:23]1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:23][C:3]1[C:2]([C:16](=[O:18])[CH3:17])=[CH:11][C:10]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Komponenten

Reaktionsbedingungen

Temperatur: 122 °C

Versuchsvorschrift

A mixture of methyl 3-bromo-5-(methylsulfonyl)benzoate (66 mg, 0.226 mmol), 1-(vinyloxy)butane (45.3 mg, 0.06 mL, 0.452 mmol), palladium acetate (1.5 mg, 0.0068 mmol), DPPP (6.1 mg, 0.015 mmol) and potassium carbonate (37.5 mg, 0.27 mmol) in DMF (0.6 mL) and H2O (0.07 mL) in a Smith process vial was heated at 122° C. in microwave for 3 h. The reaction mixture was cooled down to room temperature and hydrolyzed by addition of 5% HCl (1 mL) slowly. The reaction mixture was worked up by extraction with ethyl acetate and concentration under vacuum. The crude mixture was purified by reverse phase prep HPLC to give the title compound (16 mg): 1H NMR (CD3OD, 500 MHz) δ ppm 2.74 (3H, s), 3.24 (3H, s), 8.70 (1H, m), 8.75 (1H, m), 8.87 (1H, m). HPLC retention time: 1.037 min (method A). MS (ESI) (M+H)+ 243.10.

Aufarbeitung

extractionThe reaction mixture was worked up by extraction with ethyl acetate and concentration under vacuum
customThe crude mixture was purified by reverse phase prep HPLC

Quellen und Nachweise

ORD-Eintrag: ord-cf874909ecf14dec9f8a8c08fd3450dd
Quelldatensatz: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07476764B2

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