Bromine → 8-Bromothiopyrano[3,2-b]indol-4(5H)-one

HRID 918487Notes

Reaction equation

HRID 918487 reaction equation
[S:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[C:4](=[O:14])[CH:3]=[CH:2]1.[Br:15]Br>C(O)(=O)C>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[NH:6][C:5]3[C:4](=[O:14])[CH:3]=[CH:2][S:1][C:13]=3[C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 20326608Thiopyrano[3,2-b]indol-4(5H)-one

Product 1

HCID 203266148-Bromothiopyrano[3,2-b]indol-4(5H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 8.04 g (0.04 mole) of thiopyrano[3,2-b]indol-4(5H)-one in 200 ml of acetic acid is treated dropwise with stirring at room temperature with 8.0 g (9.5 mole) of bromine. An immediate heavy precipitate formed. The mixture is concentrated to dryness and the solid residue suspended in 20 ml of pyridine and stirred for 10 minutes at 95°. The reaction mixture is poured onto ice, the solid is filtered and recrystallized from dimethylformamide, mp 334°-337°C.

Workup

  1. customAn immediate heavy precipitate formed
  2. concentrationThe mixture is concentrated to dryness
  3. additionThe reaction mixture is poured onto ice
  4. filtrationthe solid is filtered
  5. customrecrystallized from dimethylformamide, mp 334°-337°C.

Sources & evidence

ORD record
ord-e9b8c27f88e74076a22a95770064b42f
Source dataset
uspto-grants-1976_07
Patent number
US03971806

Reaction notes

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