Chlorosulfonic acid → HCID 86639363, compound

HRID 2381928Notes

Reaction equation

HRID 2381928 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[CH:5]2.[Cl:21][S:22](O)(=[O:24])=[O:23]>CC#N>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[C:5]2[S:22]([Cl:21])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 167513275-fluoro-N-tosylindole

Product 1

HCID 86639363HCID 86639363, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-fluoro-1-(toluene-4-sulfonyl)indole (5.2 g) in dry CH3CN (80 mL) is cooled in an ice-bath and treated drop wise with chlorosulfonic acid (12 mL). The reaction mixture is allowed to warm to rt and stirred for 24 h. The reaction mixture is carefully poured onto ice/water (300 mL). The precipitate is collected by filtration and washed with water to afford 5-fluoro-3-chlorosulfonyl-1-(toluene-4-sulfonyl)-1H-indole (6.8 g, 98%) as a solid. MS: 386 (M−H).

Workup

  1. additionThe reaction mixture is carefully poured onto ice/water (300 mL)
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-aa24762146f84d24adbc5d314c77c3dc
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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