Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1) → 1-Fluoro-2-(4-methylsulfonylphenyl)-3-phenylazulene

HRID 1456825Notes

Reaction equation

HRID 1456825 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:20]=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[O-]S(C(F)(F)[F:32])(=O)=O.F[N+]1C=CC=CC=1>ClCCCl>[F:32][C:20]1[C:19]2[C:13]([CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11]=1[C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 2724576Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1)HCID 221071632-(4-Methylsulfonylphenyl)-1-phenylazulene

Product 1

HCID 221071841-Fluoro-2-(4-methylsulfonylphenyl)-3-phenylazuleneYield 47.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-(4-methylsulfonylphenyl)-1-phenylazulene (0.20 g) in 1, 2-dichloroethane (20.0 ml) was added 1-fluoropyridinium triflate (0.28 g), and the reaction mixture was heated under reflux for 30 min. The mixture was poured into ice-water, and extracted with CHCl3. The combined CHCl3 extracts were washed with water and brine, dried over Na2 SO4, and concentrated. The crude product was purified by SiO2 column chromatography (benzenee/EtOAc, 20:1) to give the title compound (0.10 g) as green crystals; mp 120°-122° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 30 min
  3. extractionextracted with CHCl3
  4. washThe combined CHCl3 extracts were washed with water and brine
  5. customdried over Na2 SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by SiO2 column chromatography (benzenee/EtOAc, 20:1)

Sources & evidence

ORD record
ord-2bd214e71af34a90bffce910e2304607
Source dataset
uspto-grants-1998_12
Patent number
US05843999

Reaction notes

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