Thionyl Chloride → HCID 21458935, compound

HRID 725286Notes

Reaction equation

HRID 725286 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[C:8](Cl)[CH:9]=[CH:10][C:11]=1[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].[Mg].S(Cl)(Cl)=O.C[Si]([O:27][S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29])(C)C.[Cl-].[NH4+]>C1COCC1>[F:32][C:31]([F:34])([F:33])[S:28]([O-:30])(=[O:29])=[O:27].[C:1]([O:5][C:6]1[CH:7]=[C:8]([S+:28]([C:31]2[CH:8]=[CH:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[C:11]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=2)[C:8]2[CH:9]=[CH:10][C:11]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:7]=2)[CH:9]=[CH:10][C:11]=1[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 24386Thionyl ChlorideHCID 25517Ammonium ChlorideHCID 65367Trimethylsilyl triflateHCID 5462224MagnesiumHCID 21458933HCID 21458933, compound

Product 1

HCID 21458935HCID 21458935, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent was conventionally prepared using 51.3 g (0.2 mol) of 3,4-di-tert-butoxyphenyl chloride, 4.9 g (0.2 mol) of magnesium, and 100 g of THF. The Grignard reagent solution was cooled in an ice water bath whereupon 5.8 g (0.049 mol) of thionyl chloride diluted with 10 g of THF was added dropwise at less 30° C. Reaction mixture was ripened for about 30 minutes. Thereafter, 26.7 g (0.12 mol) of trimethylsilyltrifluoromethane sulfonate was added dropwise at less 20° C. Reaction mixture was further ripened for 1 hour and thereafter, the reaction solution was allowed to stand overnight at room temperature. After the reaction solution was again cooled in an ice water bath, 200 g of 16.7% ammonium chloride aqueous solution was added thereto at less 30° C. After separation, 100 g of chloroform was added to the organic layer, which was washed three times using 100 g of water. Thereafter, the solvent was distilled off under reduced pressure by means of a rotary evaporator, obtaining an oily residue. The oily residue was recrystallized, isolating tris(3,4-di-tert-butoxyphenyl)sulfonium trifluoromethanesulfonate of 99% purity in an amount of 13.2 g (yield 32%).

Workup

  1. additionwas added dropwise at less 30° C
  2. customReaction mixture
  3. customReaction mixture
  4. waitwas further ripened for 1 hour
  5. waitto stand overnight at room temperature
  6. temperatureAfter the reaction solution was again cooled in an ice water bath
  7. customat less 30° C
  8. customAfter separation, 100 g of chloroform
  9. additionwas added to the organic layer, which
  10. washwas washed three times
  11. distillationThereafter, the solvent was distilled off under reduced pressure by means of a rotary evaporator
  12. customobtaining an oily residue
  13. customThe oily residue was recrystallized

Sources & evidence

ORD record
ord-560e90cfefc143ef8dbd12c5ce05791d
Source dataset
uspto-grants-1998_01
Patent number
US05705702

Reaction notes

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