Trifluoroacetic acid → HCID 86694462, compound

HRID 1519547Notes

Reaction equation

HRID 1519547 reaction equation
C[C:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([F:21])[C:14]=1[Cl:22])(C([O-])=O)[C:3]([O:5][C:6](C)(C)C)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:6][O:5][C:3](=[O:4])[CH2:2][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([F:21])[C:14]=1[Cl:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131733094HCID 131733094, compound

Product 1

HCID 86694462HCID 86694462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl methyl(2-chloro-4-cyano-3-fluorophenyl)malonate (4.8 g, 15 mmol) in DCM (50 mL) was added TFA (50 mL) at room temperature and the mixture was aged for 20 hours. LC-MS and TLC (20% ethyl acetate/hexanes) indicated lack of starting malonate diester, but still some mono-acid/mono-ester intermediate. The volatiles were removed in vacuo and the residue was taken up in methanol and heated to reflux for 1 hour. The volatiles were again removed in vacuo and the residue was purified on a CombiFlash Rf (40 gm, 10-40% ethyl acetate/hexanes) to give several main fractions of clean title product by NMR. 1H-NMR (500 MHz, CDCl3) δ ppm 3.734 (s, 3H), 3.860 (s, 2H), 7.234 (d, J=8.0 Hz, 1H), 7.512 (dd, J=6.1 and 8.0 Hz, 1H).

Workup

  1. customThe volatiles were removed in vacuo
  2. temperatureheated
  3. temperatureto reflux for 1 hour
  4. customThe volatiles were again removed in vacuo
  5. customthe residue was purified on a CombiFlash Rf (40 gm, 10-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-be143779481a4ca1b1f52ebcbf333fff
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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