Phenol → HCID 58307334, compound

Temperature

110 °C

A mixture of [2-(3-fluoro-4-nitro-phenoxy)-ethyl]-dimethyl-amine (2.8 g, 12 mmol) and phenol (1.4 g, 15 mmol) in DMF (100 mL) was treated with potassium carbonate (3.4 g, 25 mmol) and the mixture heated at 110° C. under N2 with stirring. After 4 hours, the mixture was cooled to ambient temperature. The mixture was evaporated in vacuo, and the residue was partitioned between ethyl acetate (100 mL) and water (100 mL), and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic phases were washed with 10% potassium carbonate (2×100 mL) and water (2×100 mL), and were then extracted with dilute aqueous HCl (3×75 mL). The combined aqueous extracts were washed with CH2Cl2 (2×100 mL), basified (NaOH), and extracted into ethyl acetate (3×75 mL). The combined organic phases were washed with water (2×100 mL), dried (MgSO4) and evaporated, providing 3.1 g, in 84% yield; 1H NMR (CDCl3) δ 2.29 (s, 6H), 2.67 (t, J=5.8 Hz, 2H), 4.00 (t, J=5.8 Hz, 2H), 6.46 (d, J=2.6 Hz, 1H), 6.68 (dd, J=9.2 Hz, J=2.6 Hz, 1H), 7.03-7.07 (m, 2H), 7.18-7.22 (m, 1H), 7.35-7.42 (m, 2H), 8.06 (d, J=9.2 Hz, 1H).

1. temperaturethe mixture was cooled to ambient temperature
2. customThe mixture was evaporated in vacuo
3. customthe residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
4. extractionthe aqueous phase was extracted with ethyl acetate (100 mL)
5. washThe combined organic phases were washed with 10% potassium carbonate (2×100 mL) and water (2×100 mL)
6. extractionwere then extracted with dilute aqueous HCl (3×75 mL)
7. washThe combined aqueous extracts were washed with CH2Cl2 (2×100 mL)
8. extractionextracted into ethyl acetate (3×75 mL)
9. washThe combined organic phases were washed with water (2×100 mL)
10. dry with materialdried (MgSO4)
11. customevaporated
12. customproviding 3.1 g

ORD record

ord-f680a88b66594d46b135d10ac12a2693

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481568B2