Trifluoroacetic acid → HCID 54108731, compound

A solution of 2-fluoro-3-methoxyphenyl)-3-oxo-propanoic acid from Step 1 (1.96 g, 8.6 mmol) in 4 mL of trifluoroacetic acid and 2 mL of trifluoroacetic anhydride was stirred at room temperature for 1 hour. The solution was concentrated in vacuo, the residue dissolved in ether, and the ethereal solution was washed with saturated aqueous NaHCO3, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give a solid that was purified by flash chromatography to provide 0.37 g (32%) of the desired ketone. The aqueous phase from the NaHCO3 was acidified, extracted with ether, washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide 1.13 g, of recovered 2-fluoro-3-methoxyphenyl)-3-oxo-propanoic acid: mp 112°-118° C.; 1H NMR (CDCl3 /300 MHz) 7.86 (dd, J=8.66, 1.41 Hz, 1H), 7.00 (apparent t, J=8.26 Hz, 1H), 4.96 (s, 2H), 4.31 (S, 2H), 3.97 (S, 3H); 19F NMR (CDCl3 /282 MHz) -142.2 (d). Mass spectrum M+ =196.

1. concentrationThe solution was concentrated in vacuo
2. dissolutionthe residue dissolved in ether
3. washthe ethereal solution was washed with saturated aqueous NaHCO3, brine
4. dry with materialdried over anhydrous MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a solid
8. customthat was purified by flash chromatography

ORD record

ord-5b04758a60b7443e84ec78ce66848981

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05565482