Toluene → 9-Phenylcarbazole

HRID 917803

Reaktionsgleichung

Reaktionsgleichung von HRID 917803
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]Cl.C(O)(=O)C.C(N(CC)CC)C.C(#N)C.O.O>[C:15]1([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

11

Edukt 4

HCID 1140TolueneHCID 6854CarbazoleHCID 7961BromobenzeneHCID 10340Sodium Carbonate

Produkt 1

HCID 708519-Phenylcarbazole

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 62652Cuprous chlorideKatalysatorHCID 164911Tetraphenylphosphonium ChlorideKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
52.5 °C

Versuchsvorschrift

Carbazole was mixed in an amount of 16.47 g (98.52 mmol) with 31.0 g (197.04 mmol) of bromobenzene, 10.44 g (98.52 mmol) of sodium carbonate, 0.4 g (8.0 mmol) of copper-(I) chloride, and 3.0 g (8.0 mmol) of tetraphenylphosphonium chloride. This mixture was reacted at 115-125° C. for 2 hours in a nitrogen stream. After the reaction, 50 mL of toluene and 100 mL of water were added and the resultant mixture was subjected to liquid separation. Thereafter, the organic layer was washed with water and dried with anhydrous sodium sulfate. After the drying agent was removed by filtration, 15.6 g of activated clay was added. The resultant mixture was stirred at 50-55° C. for 1 hour and the clay was removed by filtration. The toluene was concentrated under reduced pressure and 352 mL of methanol was added to the residue. The resultant solution was subjected to crystallization. Thus, the target compound (I-27) was obtained as white crude crystals in an amount of 22.7 g (yield, 94.8%). The target compound obtained had a melting point of 96-97° C. and a content as determined by HPLC of 99.8% (HPLC conditions: column, ODS-80TM; eluent, acetonitrile/water (V/V=65/35); buffer, triethylamine and acetic acid each in an amount of 0.1%; detection UV, 254 nm; flow rate, 1.0 mL/min)

Aufarbeitung

  1. customThis mixture was reacted at 115-125° C. for 2 hours in a nitrogen stream
  2. additionwere added
  3. customthe resultant mixture was subjected to liquid separation
  4. washThereafter, the organic layer was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customAfter the drying agent was removed by filtration, 15.6 g of activated clay
  7. additionwas added
  8. customthe clay was removed by filtration
  9. concentrationThe toluene was concentrated under reduced pressure and 352 mL of methanol
  10. additionwas added to the residue
  11. customThe resultant solution was subjected to crystallization
  12. customThus, the target compound (I-27) was obtained as white crude crystals
  13. customin an amount of 22.7 g (yield, 94.8%)
  14. customThe target compound obtained

Quellen und Nachweise

ORD-Eintrag
ord-98518565e6424e62aadd258f4d6a9b12
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273953B2

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