2,2,2-Trifluoroethanol → HCID 68153597, compound

To a solution of 2,2,2-trifluoroethanol (874 μL, 12.0 mmol) at 0° C. was added NaH (60%, 520 mg, 13.0 mmol) and the mixture was stirred at this temp for 10 min, then at room temperature for 10 min. The mixture was cooled to 0° C. before methyl 4-(bromomethyl)-3-methoxybenzoate (2.59 g, 10.0 mmol) was added. The cooling bath was removed and the mixture was stirred at room temperature for 3 hours. The mixture was poured into water and extracted with EtOAc (3×). The organics were combined, washed with water, brine, dried (MgSO4) and evaporated to dryness. Crushed NaOH was added to the residue, followed by water (4 mL) and MeOH (20 mL). The mixture was stirred at room temperature for 1 hour. The MeOH was evaporated and the residue was taken up in 1N NaOH (30 ml) and the pH was adjusted to pH 2 with conc HCl. The precipitate was filtered, washed with water (2×) then hexanes (2×) and desiccated to give 3-methoxy-4-((2,2,2-trifluoroethoxy)methyl)benzoic acid. 1H NMR (400 MHz, CDCl3) δ 7.79 (dd, J=7.8, 1.4 Hz, 1H), 7.61 (d, J=1.4 Hz, 1H), 7.53 (d, J=7.8 Hz, 1H), 4.80 (s, 2H), 4.00-3.91 (m, 5H).

1. waitat room temperature for 10 min
2. additionwas added
3. customThe cooling bath was removed
4. stirringthe mixture was stirred at room temperature for 3 hours
5. additionThe mixture was poured into water
6. extractionextracted with EtOAc (3×)
7. washwashed with water, brine
8. dry with materialdried (MgSO4)
9. customevaporated to dryness
10. additionCrushed NaOH was added to the residue
11. stirringThe mixture was stirred at room temperature for 1 hour
12. customThe MeOH was evaporated
13. filtrationThe precipitate was filtered
14. washwashed with water (2×)

ORD record

ord-2b5774c02d1a430d9a2f85a1d0d4e0ec

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916565B2