Methyl triflate → HCID 18780403, compound

HRID 1421203Notes

Reaction equation

HRID 1421203 reaction equation
[CH2:1]([S:5][C:6]1[C:7]2[C:12]([CH:13]=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]3)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].[F:20][C:21]([F:28])([F:27])[S:22]([O:25]C)(=[O:24])=[O:23]>CCCCCCC>[O-:25][S:22]([C:21]([F:28])([F:27])[F:20])(=[O:24])=[O:23].[CH:18]1[C:19]2[C:14](=[CH:13][C:12]3[C:7]([C:6]=2[S+:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH3:21])=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 10858424Anthracene, 9-(butylthio)-

Product 1

HCID 18780403HCID 18780403, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

10.0 g (37.5 mM) of 9-butylthioanthracene was dissolved in approximately 100 mL heptane. To this was slowly added 6.2 g (4.3 mL, 37.8 mM) of methyl trifluoromethanesulfonate. There was a slight color change due to local orange color produced on addition, no exotherm, and haziness after a short time. The reaction was left to stir over the weekend during which time a precipitate formed. The reaction was cooled in an ice bath, then filtered and rinsed with hexanes, then air dried. This material was recrystallized from IPA, filtered, then dried in a 65° C. vacuum oven overnight to yield 2.7 g of 9-anthryl n-butyl methyl sulfonium triflate.

Workup

  1. customproduced on addition
  2. waitThe reaction was left
  3. customformed
  4. temperatureThe reaction was cooled in an ice bath
  5. filtrationfiltered
  6. washrinsed with hexanes
  7. customair dried
  8. customThis material was recrystallized from IPA
  9. filtrationfiltered
  10. customdried in a 65° C. vacuum oven overnight

Sources & evidence

ORD record
ord-c4ec74b8777c46408bc99dbf8c184975
Source dataset
uspto-grants-2000_06
Patent number
US06074800

Reaction notes

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