反应详情

温度

100 °C

A solution of methyl 2-hydroxy-4-iodobenzoate (50 g, 0.18 mol) [Aldrich, 652636] in acetic acid (360 mL) was treated with N-chlorosuccinimide (29 g, 0.22 mol) and heated at 100° C. for 1 hour. The reaction mixture was cooled until the internal temperature was 19° C. and then the solid that precipitated was filtered, washed with cold acetic acid, and air dried. The solid was diluted with toluene and concentrated (2×200 mL) to remove residual acetic acid to give 34.8 g of the desired product. The filtrate was concentrated, and the residue was purified by flash column chromatography using ethyl acetate in hexanes (0%-20%) to give an additional 8.6 g of desired product (total yield=43 g, 77%). LCMS for C8H7ClIO3 (M+H)+: m/z=312.9; Found: 313.0.

1. temperatureThe reaction mixture was cooled until the internal temperature
2. customwas 19° C.
3. customthe solid that precipitated
4. filtrationwas filtered
5. washwashed with cold acetic acid, and air
6. customdried
7. additionThe solid was diluted with toluene
8. concentrationconcentrated (2×200 mL)
9. customto remove residual acetic acid