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

HRID 1396052Notes

Reaction equation

HRID 1396052 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([Br:18])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])[CH3:7]>>[C:6]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([Br:18])=[C:15]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])[CH3:7]

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 chlorideYield 93%

Conditions

Temperature
70 °C

Procedure

Under N2 atmosphere, 25.00 mL chlorosulfonic acid was cooled in an ice bath, and under stirring 5.00 g 1-acetyl-5-bromoindoline was added portionwise. Stirring was continued for 20 min. after which the ice bath was removed and the mixture was heated to 70° C. After cooling to room temperature, the mixture was cautiously poured into ice water and extracted twice with DCM. The combined organic layers were dried over MgSO4 and evaporated to dryness to give 6.57 g (93%) of a beige solid. 1H NMR (400 MHz, DMSO-d6) δ 2.16 (s, 3H), 3.15 (t, J=8.58 Hz, 2H), 4.11 (t, J=8.58 Hz, 2H), 7.37 (s, 1H), 8.66 (s, 1H).

Workup

  1. additionwas added portionwise
  2. customafter which the ice bath was removed
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture was cautiously poured into ice water
  5. extractionextracted twice with DCM
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-ecce29acd8f4454a862a1933793fd80b
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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