Potassium Carbonate → Bromo-7-methoxy-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one
Reaktionsgleichung
CO[C:3](=[O:14])[C:4]1[C:9](C)=[CH:8][C:7](Br)=[CH:6][C:5]=1[CH2:12][Br:13].[F:15][C:16]([F:27])([F:26])[O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.[C:28]([O-])([O-])=[O:29].[K+].[K+]>C1(C)C=CC=CC=1>[Br:13][CH:12]1[C:5]2[C:4](=[C:9]([O:29][CH3:28])[CH:8]=[CH:7][CH:6]=2)[C:3](=[O:14])[N:23]1[CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][C:16]([F:26])([F:27])[F:15])=[CH:19][CH:20]=1Komponenten
5
Versuchsvorschrift
4-Bromo-2-bromomethyl-6-methylbenzoic acid methyl ester (762 mg, 2.37 mmol), 4-trifluoromethoxy benzylamine (0.543 mL, 3.56 mmol) and K2CO3 (981 mg, 7.10 mmol) were stirred in toluene (10 mL) at 95° C. for 12 hours. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the product was purified by column chromatography (10-25% EtOAc/Hexanes) to afford a yellow oil (650 mg, 66%). 1H NMR (300 MHz, CDCl3): δ 7.33-7.36 (m, 2H), 7.18 (d, 2H), 7.13 (s, 1H), 7.07 (s, 1H), 4.75 (s, 2H), 4.22 (s, 2H), 4.00 (s, 3H).
Aufarbeitung
- customThe reaction was partitioned between ethyl acetate and water
- washthe organic layer was washed with brine
- dry with materialdried over anhydrous Na2SO4
- customThe solvent was removed under reduced pressure
- customthe product was purified by column chromatography (10-25% EtOAc/Hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-c8891f0104c14584ad0b668e5f99363b
- Quelldatensatz
- uspto-grants-2011_06
- Patentnummer
- US07968570B2
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