Selectfluor → HCID 89306362, compound

HRID 587219Notes

Reaction equation

HRID 587219 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:23]([F:26])([F:25])[F:24])/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[C:18](=[O:22])[CH2:17][CH2:16]3)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].[B-](F)(F)(F)[F:28].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:23]([F:25])([F:26])[F:24])/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[C:18](=[O:22])[CH:17]([F:28])[CH2:16]3)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 86675155HCID 86675155, compound

Product 1

HCID 89306362HCID 89306362, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (E)-5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2,3-dihydro-1H-inden-1-one (0.5 g, 1.24 mmol) in MeCN (20 mL), was added Selectfluor® (0.52 g, 1.48 mmol) and the reaction was heated to reflux temperature for 16 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure and diluted with CH2Cl2. The solution was washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude product which was purified by flash column chromatography (SiO2, 100-200 mesh; 15% EtOAc in petroleum ether) to afford the title compound as a pale yellow semi solid (0.1 g, 24%): 1H NMR (400 MHz, CDCl3) δ 7.80 (m, 1H), 7.48 (m, 2H), 7.32 (m, 2H), 6.65 (d, J=16.0 Hz, 1H), 6.54 (dd, J=16.0, 8.0 Hz, 1H), 5.38 (m, 1H), 4.18 (m, 1H), 3.62 (m, 1H), 3.32 (m, 1H); ESIMS m/z 419.06 ([M−H]−); IR (thin film) 1728, 1114, 817 cm−1.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux temperature for 16 h
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with CH2Cl2
  5. washThe solution was washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product which
  9. customwas purified by flash column chromatography (SiO2, 100-200 mesh; 15% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-9969becbb3414c9096081bfd31343ff1
Source dataset
uspto-grants-2016_01
Patent number
US09226500B2

Reaction notes

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