N-bromobutanimide → 5-Bromo-2-oxindole

HRID 1797211Notes

Reaction equation

HRID 1797211 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].C1C(=O)N([Br:18])C(=O)C1>C(#N)C>[Br:18][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:10])[CH2:3]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 321710Oxindole

Product 1

HCID 6111935-Bromo-2-oxindole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-10 °C

Procedure

Oxindole (1.30 g, 0.010 mmol) was suspended in dry acetonitrile (22.0 mL) under N2 and cooled to −10° C. To this stirred mixture was added recrystallized NBS (2.00 g, 0.011 mol) portionwise. The resulting suspension was stirred at −10 to 10° C. for 3 h. The precipitated solid was collected by filtration, washed with H2O and dried to give the intermediate title compound as an off white solid 1.75 g (82%). Electrospray mass spectrum (M−1)=210, (M−1)=211

Workup

  1. additionTo this stirred mixture was added
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with H2O
  4. customdried

Sources & evidence

ORD record
ord-1e563492ef1c4af688a5b994fc3b2ac8
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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