Chlorosulfonic acid → 1-acetyl-5-bromo-2,3-dihydro-1H-indole-6-sulfonyl chloride

HRID 2290182Notes

Reaction equation

HRID 2290182 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11](=[O:13])[CH3:12])[CH2:6][CH2:5]2.[Cl:14][S:15](O)(=[O:17])=[O:16]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:15]([Cl:14])(=[O:17])=[O:16])[N:7]([C:11](=[O:13])[CH3:12])[CH2:6][CH2:5]2

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 7218471-(5-bromo-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Product 1

HCID 140245841-acetyl-5-bromo-2,3-dihydro-1H-indole-6-sulfonyl chloride

Conditions

Temperature
0 °C

Procedure

To 5-bromo-N-acetylindoline 122.86 g (0.51 mol) cooled in an ice bath was added chlorosulfonic acid, 116.52 g (2.6 moles) very cautiously. The mixture was stirred for about 30 minutes at 0° C. and then allowed to warm to room temperature. The mixture was then heated slowly to about 70°-90° C. overnight. After cooling, the cold solution was slowly added to ice and the solids collected by suction filtration, washed several times with water and allowed to dry overnight. The product was recrystallized from chloroform to give 72.5 g (42% by weight yield) of 5-bromo-6-chlorosulfonyl-N-acetylindoline.

Workup

  1. temperatureto warm to room temperature
  2. temperatureThe mixture was then heated slowly to about 70°-90° C. overnight
  3. temperatureAfter cooling
  4. additionthe cold solution was slowly added to ice
  5. filtrationthe solids collected by suction filtration
  6. washwashed several times with water
  7. customto dry overnight
  8. customThe product was recrystallized from chloroform

Sources & evidence

ORD record
ord-eb737f28619e4bac81466e0164103389
Source dataset
uspto-grants-1986_10
Patent number
US04615966

Reaction notes

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