N-Iodosuccinimide → HCID 86666943, compound

Temperature

90 °C

A solution of 1-(4,5-dichloro-2-hydroxyphenyl)ethanone (12 g, 59 mmol) in acetic acid (70 mL) was treated with N-iodosuccinimide (16 g, 71 mmol) and stirred at 90° C. for 18 h. The reaction mixture was treated with additional N-iodosuccinimide (8 g, 36 mmol) and stirred at 90° C. for 4 h. The reaction mixture was concentrated, diluted with ethyl acetate, and quenched with saturated sodium bicarbonate until the bubbling stopped. The organic layer was separated and the aqueous was re-extracted with ethyl acetate. The combined organic layers were dried and concentrated to give a brown solid. This material was recrystallized from methanol to give desired product (9.0 g, 46%) as a tan solid. 1H NMR (300 MHz, CDCl3) δ 13.36 (s, 1H), 7.85 (s, 1H), 2.65 (s, 3H). LCMS for C8H6Cl2IO2 (M+H)+: m/z=330.9, 332.9; Found: 330.8, 332.9.

1. stirringstirred at 90° C. for 4 h
2. concentrationThe reaction mixture was concentrated
3. additiondiluted with ethyl acetate
4. customquenched with saturated sodium bicarbonate until the bubbling
5. customThe organic layer was separated
6. extractionthe aqueous was re-extracted with ethyl acetate
7. customThe combined organic layers were dried
8. concentrationconcentrated
9. customto give a brown solid
10. customThis material was recrystallized from methanol

ORD record

ord-f1b2ffd3fb8246fcb955f6a9750ea57c

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199982B2