Bromine → 5-Bromo-2-fluoro-4-hydroxybenzaldehyde

Temperature

45 °C

To a solution of 2-fluoro-4-hydroxybenzaldehyde (2.2 g, 15.7 mmol, 1 eq) in acetic acid (70 mL) was added a solution of bromine (2.71 g, 17.0 mmol, 1.1 eq) in acetic acid (10 mL), and the mixture was stirred at 45° C. for 26 h. The reaction was concentrated in vacuo, brine (50 mL) was added, and the mixture was extracted with EtOAc (3×80 mL). The combined organic layers were dried (Na2SO4), concentrated in vacuo. The resultant residue was purified by silica gel chromatography (DCM:MeOH=15:1 to 5:1) to afford 1.2 g (35%) of 5-bromo-2-fluoro-4-hydroxybenzaldehyde (25).

1. concentrationThe reaction was concentrated in vacuo, brine (50 mL)
2. additionwas added
3. extractionthe mixture was extracted with EtOAc (3×80 mL)
4. dry with materialThe combined organic layers were dried (Na2SO4)
5. concentrationconcentrated in vacuo
6. customThe resultant residue was purified by silica gel chromatography (DCM:MeOH=15:1 to 5:1)

ORD record

ord-86b166b84f3a4470880b3752f6023d13

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822467B2