Ethyl Acetate → 2-broMo-5-hydroxybenzoic acid Methyl ester

To a solution of compound methyl 2-bromo-5-methoxybenzoate (100 g, 410 mmol) in DCM (2000 mL) was added and BBr3 (1N, 150 mL) at −78° C. under N2 The mixture was stirred at 0° C. under N2 for 24 hr. The reaction was quenched with MeOH (500 mL), concentrated to dryness, diluted with H2O (50 mL), and extracted with ethyl acetate (800 mL*3), The organic phase was washed with saturated sodium bicarbonate solution 50 mL, dried over Na2SO4. After concentration, the crude product was purified by silica gel chromatography eluted with PE:EA=1:1 to give title product (80 g, 85% yield) as yellow oil. LCMS (10-80 AB—2MIN.M): Rt=0.820, purity=85%, M+1=231.

1. customThe reaction was quenched with MeOH (500 mL)
2. concentrationconcentrated to dryness
3. additiondiluted with H2O (50 mL)
4. extractionextracted with ethyl acetate (800 mL*3)
5. washThe organic phase was washed with saturated sodium bicarbonate solution 50 mL
6. dry with materialdried over Na2SO4
7. concentrationAfter concentration
8. customthe crude product was purified by silica gel chromatography
9. washeluted with PE

ORD record

ord-29fc69348a3240118fea816ab2585606

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029391B2