Trifluoroacetic acid → 5-(5-chloro-2-fluorophenyl)-3-methyl-3-phenyl-2,3-dihydroisoxazole

HRID 15116Notes

Reaction equation

HRID 15116 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:31])=[C:6]([C:8]2[O:12][N:11](CC3C=CC(OC)=CC=3OC)[C:10]([CH3:30])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:9]=2)[CH:7]=1.FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:31])=[C:6]([C:8]2[O:12][NH:11][C:10]([CH3:30])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 57539120HCID 57539120, compound

Product 1

HCID 115438305-(5-chloro-2-fluorophenyl)-3-methyl-3-phenyl-2,3-dihydroisoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(5-chloro-2-fluorophenyl)-2-(2,4-dimethoxybenzyl)-3-methyl-3-phenyl-2,3-dihydroisoxazole (2-3, 0.88 g, 1.99 mmol) in anhydrous CH2Cl2 (5 mL) was added trifluoroacetic acid (5 mL) and the resulting purple colored reaction sat for 7 h. 2M Na2CO3 was added until the color changed from purple to peach, and the reaction was immediately extracted with CH2Cl2, dried with MgSO4, filtered and concentrated to provide crude 5-(5-chloro-2-fluorophenyl)-3-methyl-3-phenyl-2,3-dihydroisoxazole (2-4). This crude material was suitable for further transformations. 1H NMR (300 MHz, CDCl3) δ 7.56 (m, 3H), 7.36 (m, 3H), 7.25 (m, 1H), 7.05 (app t, J=9.6 Hz), 6.20 (br s, 1H), 6.03 (d, J=3.4 Hz, 1H), 1.78 (s, 3H). LRMS see table.

Workup

  1. customthe resulting purple colored reaction
  2. extractionthe reaction was immediately extracted with CH2Cl2
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-665a013168d14e6d94dc4c85507577d3
Source dataset
uspto-grants-2010_06
Patent number
US07732472B2

Reaction notes

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