Ethyl Bromide → HCID 86664737, compound

Temperature

70 °C

The suspension of 2-bromo-3-hydroxybenzaldehyde (120 g, 0.60 mol), K2CO3 (247 g, 1.79 mol) and bromoethane (135 mL, 1.79 mol) in DMF (700 mL) was stirred at 70° C. for 3 h. After the reaction was quenched with water (50 mL), the resulting mixture was extracted with EtOAc (3×60 mL). The combined organic layers were washed with water (50 mL) and aqueous LiCl solution (50 mL), dried over anhydrous Na2SO4 and concentrated to dryness in vacuo. The residue was purified by column chromatography on silica gel to give the target compound (128 g, yield 94%). 1H NMR (400 MHz, DMSO-d6 δ 10.45 (s, 1H), 7.52-7.50 (d, 1H), 7.38-7.34 (t, 1H), 7.13-7.10 (d, 1H), 4.18-4.13 (m, 2H), 1.53-1.50 (m, 3H).

1. customAfter the reaction was quenched with water (50 mL)
2. extractionthe resulting mixture was extracted with EtOAc (3×60 mL)
3. washThe combined organic layers were washed with water (50 mL) and aqueous LiCl solution (50 mL)
4. dry with materialdried over anhydrous Na2SO4
5. concentrationconcentrated to dryness in vacuo
6. customThe residue was purified by column chromatography on silica gel

ORD record

ord-4b8a0113701045a59e9fd42a61bd57c4

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703742B2