Water → 2,4-Dichlorobenzyl bromide

온도

80 °C

To a 500 mL round bottom flask fitted with a Teflon magnetic stirrer was added 2,4-dichlorotoluene (Aldrich) (14.4 g, 90 mmol) in 300 mL glacial acetic acid. To this was added sodium bromide (9.4 g, 92 mmol) and anhydrous ceric ammonium nitrate (100 g, 182 mmol) and the reaction mixture was heated at 80° C. for 2.5 h. The reaction mixture was then poured into 1000 g of ice and water. The slurry was extracted with ether (3×200 mL) and the combined ether layers were washed with saturated aqueous sodium bicarbonate. The organic layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure. The crude product was chromatographed by flash column chromatography on silica gel (eluted with 100% hexanes) and the desired product obtained. 1H-NMR 500 MHz (CDCl3): δ 4.58 (s, 2H), 7.28 (m, 1H), 7.43 (m, 2H),

1. customTo a 500 mL round bottom flask fitted with a Teflon magnetic stirrer
2. extractionThe slurry was extracted with ether (3×200 mL)
3. washthe combined ether layers were washed with saturated aqueous sodium bicarbonate
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. customthe solvent removed under reduced pressure
7. customThe crude product was chromatographed by flash column chromatography on silica gel (eluted with 100% hexanes)

ORD 기록

ord-a1b74c8a7974416bb8cdf3640d819c24

출처 데이터셋

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07405221B2