Benzene, 1-bromo-3-iodo- → HCID 117818174, compound

HRID 634549Notes

Reaction equation

HRID 634549 reaction equation
[C:1]1([NH:7][C:8]2[CH:20]=[CH:19][C:11]3[O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:10]=3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24](I)[CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:21][C:22]1[CH:23]=[C:24]([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[CH:20]=[CH:19][C:11]3[O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:10]=3[CH:9]=2)[CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 11561Benzene, 1-bromo-3-iodo-HCID 11776TriphenylphosphineHCID 23676156Sodium t-butoxideHCID 67204676N-phenyl-2-Dibenzofuranamine

Product 1

HCID 117818174HCID 117818174, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

N-phenyldibenzo[b,d]furan-2-amine (5.0 g, 19.3 mmol), and 1-bromo-3-iodobenzene (10.9 g, 38.6 mmol) were mixed in 100 mL of toluene. The solution was bubbled with nitrogen for 15 min. Pd(OAc)2 (0.22 g, 1.0 mmol), triphenylphosphine (0.51 g, 1.9 mmol) and sodium t-butoxide (2.2 g, 23.1 mmol) were then added. The mixture was refluxed overnight under nitrogen. After cooling, the reaction mixture was filtered through celite/silica pad and the filtrate was concentrated under vacuum. The residue was then purified by column chromatography using DCM:hexane (1:1, v/v) as the eluent. 5.6 g (71%) of a yellow solid was obtained as the product.

Workup

  1. customThe solution was bubbled with nitrogen for 15 min
  2. temperatureThe mixture was refluxed overnight under nitrogen
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through celite/silica pad
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-6397db4871bd4252b1cf2675d2fcf5ef
Source dataset
uspto-grants-2016_04
Patent number
US09324949B2

Reaction notes

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