4-Hydroxybenzaldehyde → 4-Hydroxy-3-iodobenzaldehyde

To a stirred solution of 4-hydroxybenzaldehyde (2.0 g, 16.39 mmol) in AcOH (30 mL) was added N-iodosuccinimide (4.5 g, 19.67 mmol). The reaction mixture was stirred at r.t. for 16 h, then filtered. The filtrate was poured onto water (100 mL) and EtOAc (50 mL) was added. The aqueous fraction was separated, then extracted with EtOAc (3×50 mL). The combined organic fractions were washed with water (2×20 mL), dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (2.0 g, 50%) as a white solid that was used without further purification. LCMS (ES−) 247.1 (M−H)−, RT 1.44 minutes (Method 9).

1. filtrationfiltered
2. additionThe filtrate was poured onto water (100 mL) and EtOAc (50 mL)
3. additionwas added
4. customThe aqueous fraction was separated
5. extractionextracted with EtOAc (3×50 mL)
6. washThe combined organic fractions were washed with water (2×20 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-718e7fa5c9454b87be8d036dbf026bab

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242116B2