Acetic Acid → Methyl 3-bromo-4-hydroxybenzoate

To a stirred solution of methyl 4-hydroxybenzoate (10.0 g, 84.935 mmol) in CCl4 (30 mL) was added AcOH (20 mL, 2 Vol). Br2 (1.80 mL, 71.428 mmol) was then added slowly at 0° C. After the addition was completed, the reaction mixture was brought to RT and stirred for 8 h. Reaction mixture was quenched with water (50 mL), neutralized with saturated NaHCO3 solution and extracted with EtOAc (2×150 mL). The combined organic layers were washed with water (2×50 mL) and brine (50 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to obtain crude product. The crude material was purified via silica gel column chromatography eluting with 5% EtOAc-95% hexanes to afford methyl 3-bromo-4-hydroxybenzoate (10.0 g, 66%) as a brown solid.

1. additionAfter the addition
2. customwas brought to RT
3. customReaction mixture
4. customwas quenched with water (50 mL)
5. extractionextracted with EtOAc (2×150 mL)
6. washThe combined organic layers were washed with water (2×50 mL) and brine (50 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto obtain crude product
11. customThe crude material was purified via silica gel column chromatography
12. washeluting with 5% EtOAc-95% hexanes

ORD record

ord-a49f1e927d914c5397ac6f3d8182a792

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071595B2