Bromine → HCID 20286704, compound

HRID 1112296Notes

Reaction equation

HRID 1112296 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:7]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:1][C:12]1[CH:11]=[C:10]2[C:6]([C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:9]2)=[CH:5][C:4]=1[Cl:3]

Participants

5

Reactant 3

HCID 24408BromineHCID 737953ethyl 5-chloro-3-phenyl-1H-indole-2-carboxylateHCID 23665763Sodium Bisulfite

Product 1

HCID 20286704HCID 20286704, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Add 11 ml (33 g.) of bromine to a mixture of ethyl 5-chloro-3-phenylindole-2-carboxylate (30 g.) in 100 ml of acetic acid at 10°-20°. Stir overnight and then add a solution of sodium bisulfite. Filter and wash the precipitate with water. Stir the solid with methanol and filter to yield the title compound. Recrystallization from methanol yields the analytical sample; m.p. 205°-206° C.

Workup

  1. filtrationFilter
  2. washwash the precipitate with water
  3. stirringStir the solid with methanol
  4. filtrationfilter

Sources & evidence

ORD record
ord-06a46b76273b43cea948b09ea561963e
Source dataset
uspto-grants-1978_10
Patent number
US04122034

Reaction notes

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