Carbon tetrabromide → HCID 69271647, compound

HRID 751521Notes

Reaction equation

HRID 751521 reaction equation
O[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:14]2[C:15](=[O:31])[N:16]([CH3:30])[C:17](=[O:29])[C:18]=2[C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH3:28])[CH:20]=2)[C:8]2[O:12][CH:11]=[CH:10][C:9]=2[CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:52]>ClCCl>[Br:52][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:14]2[C:15](=[O:31])[N:16]([CH3:30])[C:17](=[O:29])[C:18]=2[C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH3:28])[CH:20]=2)[C:8]2[O:12][CH:11]=[CH:10][C:9]=2[CH:13]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 69270198HCID 69270198, compound

Product 1

HCID 69271647HCID 69271647, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add to a solution of 3-[5-(2-hydroxyethoxy)benzofur-7-yl]-1-methyl-4-(1-methyl-1H-indol-3-yl)pyrrole-2,5-dione (1.87 g, 4.49 mmol) in dichloromethane (30 ml), triphenylphosphine (1.41 g, 5.39 mmol) and carbon tetrabromide (1.79 g, 5.39 mmol). Stir the reaction for 15 minutes under nitrogen atmosphere. Add another 2.2 mmol of triphenylphosphine and 2.2 mmol of carbon tetrabromide and stir for 15 more minutes. Diluted with dichloromethane, wash with water, brine, dry over magnesium sulfate, filter and concentrate. Flash chromatography over silica gel (1% methanol:dichloromethane) affords the title compound as an orange solid. MS(ES+): 479.0, 481.0.

Workup

  1. customthe reaction for 15 minutes under nitrogen atmosphere
  2. stirringstir for 15 more minutes
  3. washwash with water, brine
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-a39da547dfbf4be9ad38de519c678ae3
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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