Benzenesulfonyl chloride → Benzenesulfonic acid 7-bromo-1H-indol-5-yl ester

HRID 1766249Notes

Reaction equation

HRID 1766249 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[OH-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)(=O)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:11][S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 17980131HCID 17980131, compound

Product 1

HCID 86592475Benzenesulfonic acid 7-bromo-1H-indol-5-yl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Combine 7-bromo-5-hydroxy-1H-indole and 0.2 N NaOH (1.1 eq.) in THF. Cool to about 0° C. before adding benzenesulfonyl chloride (1.10 eq.). Allow the reaction mixture to warm to ambient temperature. After 8 hours, pour into ethyl acetate, wash with water, dry the organic layer over Na2SO4 and concentrate. Purify to give the title compound.

Workup

  1. temperatureto warm to ambient temperature
  2. washwash with water
  3. dry with materialdry the organic layer over Na2SO4
  4. concentrationconcentrate
  5. customPurify

Sources & evidence

ORD record
ord-2d00920179cb4cf3bb20f2c6379eace7
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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