Iodoethane → Ethyl 2-bromobenzoate

2-Bromobenzoic acid (2.005 g, 9.47 mmol, 1.0 eq.) was combined with iodoethane (1.60 ml, 19.9 mmol, 2.0 eq.)and sodium bicarbonate (1.68 g, 19.9 mmol, 2.0 eq.) in dimethylformamide (10 ml, 1M) and stirred at room temperature for a total of 4 days. The reaction was then diluted with water (20 ml) and extracted with ether:hexane (1:1, 3×20 ml). The combined organic extracts were washed with aqueous 10% sodium hydrogen sulfite (20 ml), water (20 ml), and aqueous saturated sodium chloride (20 ml). Next, the organic extracts were dried over sodium sulfate, filtered through magnesium sulfate and concentrated. The residue was chromatographed on silica gel (50 g) eluting with ether:hexane (1:6) to furnish the title C compound (2.17 g).

1. extractionextracted with ether:hexane (1:1, 3×20 ml)
2. washThe combined organic extracts were washed with aqueous 10% sodium hydrogen sulfite (20 ml), water (20 ml), and aqueous saturated sodium chloride (20 ml)
3. dry with materialNext, the organic extracts were dried over sodium sulfate
4. filtrationfiltered through magnesium sulfate
5. concentrationconcentrated
6. customThe residue was chromatographed on silica gel (50 g)
7. washeluting with ether:hexane (1:6)

ORD record

ord-8f9bff122816419283cb2bf409610614

Source dataset

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05374615