Bromine → 3-Bromo-5-fluoro-4-hydroxybenzaldehyde

Temperature

45 °C

To a solution of 3-fluoro-4-hydroxybenzaldehyde (2 g, 14.3 mmol, 1 eq, Oakwood Products, Inc., West Columbia, S.C., USA) in acetic acid (60 mL), was added a solution of bromine (2.7 g, 17.0 mmol, 1.2 eq) in acetic acid (10 mL), and the mixture was stirred at 45° C. for 26 h. After concentration in vacuo, brine (50 mL) was added to the residue and the mixture was extracted with EtOAc (3×80 mL). The combined organic layers were dried (Na2SO4), concentrated in vacuo, and purified by reversed phase semi-preparative .HPLC to afford 1.5 g (48%) of 3-bromo-5-fluoro-4-hydroxybenzaldehyde (26).

1. concentrationAfter concentration in vacuo, brine (50 mL)
2. additionwas added to the residue
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. custompurified by reversed phase semi-preparative .HPLC

ORD record

ord-2e1447b6899046a8ae0ab1be7967fba8

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822467B2