Oxalyl chloride → 1-Indanone, 4-bromo-

Temperatur

0 °C

4-Bromo-indan-1-one was obtained by the following procedure: A solution of 3-(2-bromo-phenyl)-propionic acid (commercially available from Oakwood Products) (15.0 g, 65.5 mmol) in CH2Cl2 at 0° C. was reacted with oxalyl chloride (7.2 mL, 1.5 eq) followed by 2-3 drops of DMF. The mixture was stirred until no more gas evolution was observed. As the mixture was concentrated and the residue was dissolved in CH2Cl2, cooled to 0° C., and treated with AlCl3 (9.6 g, 1.1 eq). After 1 h the mixture was quenched with water and the layers were separated. The aqueous layer was extracted with Et2O (3×150 mL) and the combined organic extracts were washed with H2O (3×100 mL), saturated NaHCO3 (3×100 mL), brine (1×100 mL), dried over MgSO4 and concentrated. 4-Bromoindan-1-one, 10.5 g (76%) was obtained by chromatography using 10% EtOAc:hexane as eluant. Use of 4-bromo-indan-1-one in Method NINETEEN produced 4-(4-bromo-indan-2-yl)-1,3-dihydro-imidazole-2-thione (Compound 149).

1. concentrationAs the mixture was concentrated
2. dissolutionthe residue was dissolved in CH2Cl2
3. customAfter 1 h the mixture was quenched with water
4. customthe layers were separated
5. extractionThe aqueous layer was extracted with Et2O (3×150 mL)
6. washthe combined organic extracts were washed with H2O (3×100 mL), saturated NaHCO3 (3×100 mL), brine (1×100 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated

ORD-Eintrag

ord-543de17566d64a0daa1a055afa83368e

Quelldatensatz

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07419994B2