Trifluoromethanesulfonyl chloride → HCID 13826402, compound

HRID 1906915Notes

Reaction equation

HRID 1906915 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([OH:12])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:13].[F:14][C:15]([F:21])([F:20])[S:16](Cl)(=[O:18])=[O:17]>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][S:16]([C:15]([F:21])([F:20])[F:14])(=[O:18])=[O:17])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:13]

Participants

4

Reactant 2

HCID 79000Trifluoromethanesulfonyl chlorideHCID 970831HCID 970831, compound

Product 1

HCID 13826402HCID 13826402, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,6-Dichloro-7-hydroxyindan-1-one (21.71 g., 0.1 mole) was dissolved in DMF (80 ml) in a dry apparatus under nitrogen. Trifluormethanesulfonylchloride (21.60 g., 0.128 mole) was added with stirring, slowly, dropwise over a 20 minute period with occasional cooling to keep the internal temperature below 30° C. After the addition was complete, the reaction was stirred at room temperature for 30 minutes, then poured into ice-water with swirling. The green crystals were collected, washed with water, sucked dry, then dried in a vacuum oven at 50° C. to give 32.7 g. of the title compound mp 96°-100° C. Recrystallization from hexanes gave 22.4 g., mp 96°-98° C. A sublimed sample had mp 90°-96° C.

Workup

  1. temperatureslowly, dropwise over a 20 minute period with occasional cooling
  2. customthe internal temperature below 30° C
  3. additionAfter the addition
  4. stirringthe reaction was stirred at room temperature for 30 minutes
  5. customThe green crystals were collected
  6. washwashed with water
  7. customsucked dry
  8. customdried in a vacuum oven at 50° C.
  9. customto give 32.7 g

Sources & evidence

ORD record
ord-c38271c510864944bd227311757e22f9
Source dataset
uspto-grants-1987_03
Patent number
US04654363

Reaction notes

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