Potassium Hydroxide → 5-Nitro-6-(2,4-difluorophenylthio)-1-indanone ethylene ketal

HRID 1267810Notes

Reaction equation

HRID 1267810 reaction equation
[CH2:1]1[O:17][C:4]2([C:12]3[C:7](=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[C:10](Br)[CH:11]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[SH:26].[OH-].[K+]>N1C=CC=CC=1.O>[CH2:1]1[O:17][C:4]2([C:12]3[C:7](=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[C:10]([S:26][C:20]4[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=4[F:18])[CH:11]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 27370732,4-Difluorobenzene-1-thiolHCID 10357417HCID 10357417, compound

Product 1

HCID 103167575-Nitro-6-(2,4-difluorophenylthio)-1-indanone ethylene ketalYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a mixture of 5-nitro-6-bromo-1-indanone ethylene ketal (600 mg, 2.0 mmol) and 2,4-difluorothiophenol (F. Klages and K. Bott Chem. Ber. 97,735 (1964)) (440 mg, 3.0 mmol) in pyridine (4.0 mL) was added a solution of 8M aqueous potassium hydroxide (375 μL, 3.0 mmol) at room temperature. The mixture was stirred for 2 h, diluted with water and extracted with ethyl acetate. The ethyl acetate extract was washed successively with 1M aqueous NaOH (2x),0.5M aqueous HCl (1x), brine, dried over anhydrous MgSO4 and concentrated in vacuo. Chromatography over silica gel and eluted with toluene: ethyl acetate (10:1) afforded the title compound (590 mg, 81%) as a pale yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed successively with 1M aqueous NaOH (2x),0.5M aqueous HCl (1x), brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. washChromatography over silica gel and eluted with toluene: ethyl acetate (10:1)

Sources & evidence

ORD record
ord-733c2cb8f602483390d7489c6ce37321
Source dataset
uspto-grants-2003_04
Patent number
USRE038103E1

Reaction notes

Loading…