Hydrochloric Acid → 3-(5-Bromo-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

HRID 1829047

Reaction equation

HRID 1829047 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].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.[Br:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:32](=O)[O:31][CH2:30]2.Cl>C(COC)OC.O.C1COCC1>[Br:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:32](=[C:3]1[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]1=[O:10])[O:31][CH2:30]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 321710OxindoleHCID 6031445-BromophthalideHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 696592423-(5-Bromo-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-oneYield 77.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of oxindole (3.13 g, 23.5 mmol) in anhydrous dimethoxyethane (20 ml) under nitrogen was added 1.0M LiHMDS/THF solution (49 ml, 49 mmol). The mixture was stirred at room temperature for 10 minutes, and 5-bromophthalide (3.00 g, 14.1 mmol) was added. The reaction mixture was stirred at room temperature for 3 hours and then poured into a mixture of THF (50 ml) and 2M HCl aqueous solution (50 ml). After heated at reflux for 1 hour and then cooled to room temperature, the resulting mixture was poured into water (100 ml). The resulting solid was filtered, washed with water and dried under vacuum to give 3-(5-bromo-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one as a yellow solid (3.57 g, 77%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. temperatureAfter heated
  3. temperatureat reflux for 1 hour
  4. temperaturecooled to room temperature
  5. filtrationThe resulting solid was filtered
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-fd1637c97421450eac1d5663cb8762fa
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Linked notes

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