Toluene → 7-(3-(Pyren-1-yl)phenyl)dibenzo[c,h]acridine

HRID 576492Notes

Reaction equation

HRID 576492 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:21]3[CH:20]=[CH:19][C:18]4[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=4[C:16]=3[N:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]2[CH:29]=[CH:28][CH:27]=[CH:26][C:13]=23)[CH:5]=[CH:6][CH:7]=1.[C:30]1(B(O)O)[C:43]2[C:44]3=[C:45]4[C:40](=[CH:41][CH:42]=2)[CH:39]=[CH:38][CH:37]=[C:36]4[CH:35]=[CH:34][C:33]3=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C(O)C>[C:30]1([C:2]2[CH:3]=[C:4]([C:8]3[C:21]4[CH:20]=[CH:19][C:18]5[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=5[C:16]=4[N:15]=[C:14]4[C:9]=3[CH:10]=[CH:11][C:12]3[CH:29]=[CH:28][CH:27]=[CH:26][C:13]=34)[CH:5]=[CH:6][CH:7]=2)[C:43]2[C:44]3=[C:45]4[C:40](=[CH:41][CH:42]=2)[CH:39]=[CH:38][CH:37]=[C:36]4[CH:35]=[CH:34][C:33]3=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 5084102Pyren-1-ylboronic acidHCID 866914847-(3-Bromophenyl)dibenzo[c,h]acridine

Product 1

HCID 866914837-(3-(Pyren-1-yl)phenyl)dibenzo[c,h]acridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

10 (700 mg, 1.61 mmol), pyren-1-ylboronic acid (434 mg, 1.76 mmol), Palladium tetrakis triphenylphoshine (186 mg, 0.16 mmol) and potassium carbonate (1.34 g, 9.66 mmol) were introduced in a flask together with 17 mL toluene, 8.8 mL ethanol and 2.6 mL distilled water. This mixture is stirred at 80° C. during 24 hours before being filtered. The solid is then washed with hexane, water and some mL of chloroform before being dried.

Workup

  1. distillationdistilled water
  2. filtrationbefore being filtered
  3. washThe solid is then washed with hexane, water
  4. dry with materialsome mL of chloroform before being dried

Sources & evidence

ORD record
ord-094653e44f9d463c924ca799891b9f16
Source dataset
uspto-grants-2015_05
Patent number
US09040175B2

Reaction notes

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