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

HRID 1475319Notes

Reaction equation

HRID 1475319 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][C:5]2([CH3:15])[CH3:14].[Cl:16][S:17](O)(=[O:19])=[O:18]>>[C:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[C:10]([S:17]([Cl:16])(=[O:19])=[O:18])[CH:9]=2)[C:5]([CH3:15])([CH3:14])[CH2:6]1)(=[O:13])[CH3:12]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 161154361-(5-Bromo-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone

Product 1

HCID 867239431-Acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonyl chloride

Procedure

1-(5-Bromo-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone (2.0 g, 7.5 mmol) was slowly added to chlorosulfonic acid (20 mL) and the resulting solution was stirred at room temperature for 3 days. The mixture was then carefully poured over ice and the resulting solid filtered, washed with water and dried in vacuo to give the title compound (2.7 g) as a pale brown solid. 1H NMR (Acetone-d6): 9.02 (1H, s), 7.89 (1H, s), 4.11 (2H, s), 2.26 (3H, s), 1.49 (6H, s).

Workup

  1. additionThe mixture was then carefully poured over ice
  2. filtrationthe resulting solid filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-60083a739a5b4663b7ca23000a54a28b
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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