Acetic Acid → 1-Acetyl-5-bromo-6-hydroxyindoline

HRID 1870902Notes

Reaction equation

HRID 1870902 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(O)(=O)C.[Br:18]N1C(=O)CCC1=O>CN(C=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:18])=[C:10]([OH:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 186942471-(6-Hydroxyindolin-1-YL)ethanone

Product 1

HCID 186942931-Acetyl-5-bromo-6-hydroxyindolineYield 73.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
12.5 °C

Procedure

A stirred suspension of finely powdered 1-acetyl-6-hydroxyindoline (D63, 2.4 g, 0.013 mole) in a mixture of DMF (25 ml) and glacial acetic acid (125 ml) at 15° C. was treated portionwise over 5 minutes with N-bromosuccinimide (2.65 g, 0.015 mole). The reaction mixture changed from yellow to grey-green in colour. The mixture was stirred at 1 5-20° C. for 45 minutes, then cooled to 5° C. and the solid filtered off, washed with acetic acid and dried to give the title compound as a grey solid (2.45 g, 71%).

Workup

  1. temperaturecooled to 5° C.
  2. filtrationthe solid filtered off
  3. washwashed with acetic acid
  4. customdried

Sources & evidence

ORD record
ord-014d8f889d69489c82a1e2ca100c930d
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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