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

HRID 1475306Notes

Reaction equation

HRID 1475306 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]>>[C:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[C:10]([S:15]([Cl:14])(=[O:17])=[O:16])[CH:9]=2)[CH2:5][CH2:6]1)(=[O:13])[CH3:12]

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

Procedure

1-(5-Bromo-2,3-dihydro-indol-1-yl)-ethanone (0.249 g, 1.04 mmol) was added portionwise to chlorosulfonic acid (1 mL) at 20° C. with stirring and mixture was stirred for 26 h, then poured onto crushed ice. The resulting solid was collected by filtration and dried in vacuo. The filtrate was extracted with EtOAc and the organic phase was dried (Na2SO4) and evaporated in vacuo to give further solid. The two batches of solid were combined to give the title compound (0.25 g) which was used in the next stage without further purification. MS: [M−H]−=336.

Workup

  1. stirringmixture was stirred for 26 h
  2. additionpoured
  3. customonto crushed ice
  4. filtrationThe resulting solid was collected by filtration
  5. customdried in vacuo
  6. extractionThe filtrate was extracted with EtOAc
  7. dry with materialthe organic phase was dried (Na2SO4)
  8. customevaporated in vacuo
  9. customto give further solid

Sources & evidence

ORD record
ord-1e72ac46393a4772a7eb38f8389cb7ab
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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