Acetonitrile → 5-Bromo-3-fluoro-2-hydroxybenzaldehyde

This material was prepared as reported in J. Molecular Catalysis A, 2007, 30-33. Commercial 3-fluoro-2-hydroxybenzaldehyde (0.280 g, 2 mmol) was dissolved in MeCN (10 mL, 191 mmol) and ammonium acetate (0.015 g, 0.200 mmol) and NBS (0.392 g, 2.200 mmol) were added at rt. The mixture was stirred at rt for 1 h. The reaction mixture was then concentrated and the crude compound was dissolved in a small amount of dichloromethane and charged to a 12 g silica gel cartridge which was eluted with a 25 min gradient of from 0% to 30% ethyl acetate in hexanes at 30 mL/min. Fractions containing product were pooled and concentrated in vacuo to give 5-bromo-3-fluoro-2-hydroxybenzaldehyde (0.43 g, 1.963 mmol, 98% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 10.89 (s, 1H) 9.87 (s, 1H) 7.39-7.65 (m, 2H).

1. customThis material was prepared
2. concentrationThe reaction mixture was then concentrated
3. dissolutionthe crude compound was dissolved in a small amount of dichloromethane
4. additioncharged to a 12 g silica gel cartridge which
5. washwas eluted with a 25 min gradient of from 0% to 30% ethyl acetate in hexanes at 30 mL/min
6. additionFractions containing product
7. concentrationconcentrated in vacuo

ORD record

ord-4360a7e25462458aa1e37a3facfa080d

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604024B2