Methylparaben → 4-(4-Fluorophenoxy)benzoic acid

To a flask with 4-fluorophenyl boronic acid (2.1 g, 15 mmol), copper(II) acetate (1.4 g, 7.5 mmol), activated powdered molecular sieves (approximately 2 g), and methyl 4-hydroxybenzoate (1.2 g, 7.5 mmol) is added TEA (5.2 mL, 38 mmol) followed by CH2Cl2 (75 mL). The reaction is stirred for 16 hours at room temperature with air bubbling through it. The reaction mixture is diluted with CH2Cl2 and filtered through silica gel. The silica gel is washed with EtOAc-heptane. The solution is concentrated in vacuo and dissolved in dioxane (15 mL). To this solution is added aqueous LiOH (1N, 15 mL) and stirred for 18 hours at room temperature. To this reaction mixture is added aqueous HCl (1N) until acidic, having a pH less than 6. The resulting precipitate is collected by filtration and rinsed with water, and dried in vacuo to give the desired product (1.6 g, 90%). MS for C13H9FO3 (ESI) (M−H)− m/z 231.

1. custombubbling through it
2. additionThe reaction mixture is diluted with CH2Cl2
3. filtrationfiltered through silica gel
4. washThe silica gel is washed with EtOAc-heptane
5. concentrationThe solution is concentrated in vacuo
6. dissolutiondissolved in dioxane (15 mL)
7. additionTo this solution is added aqueous LiOH (1N, 15 mL)
8. stirringstirred for 18 hours at room temperature
9. additionTo this reaction mixture is added aqueous HCl (1N) until acidic,
10. filtrationThe resulting precipitate is collected by filtration
11. washrinsed with water
12. customdried in vacuo

ORD record

ord-38d679dc79f441e29133fed8c2ae02ae

Source dataset

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06479510B2