Water → HCID 86677002, compound

HRID 1473738Notes

Reaction equation

HRID 1473738 reaction equation
FC(F)(F)S(OC1C=CC2[C:31]3[C:19](=[CH:20][C:21]4[N:22]([CH2:32][CH3:33])[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=5[C:29]=4[CH:30]=3)C3C(=CC=CC=3)C=2C=1)(=O)=O.[C:36]1(B(O)O)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:32]([N:22]1[C:21]2[CH:20]=[C:19]3[C:37]4[C:36]([C:20]5[CH:21]=[C:29]([C:28]6[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=6)[CH:30]=[CH:31][C:19]=5[C:31]3=[CH:30][C:29]=2[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]1=2)=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH3:33]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86677001HCID 86677001, compound

Product 1

HCID 86677002HCID 86677002, compoundYield 135.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

10.0 g (20.28 mmol) of 10-ethyl-10H-phenanthro[9,10-b]carbazol-3-yl trifluoromethanesulfonate synthesized in Synthetic Example 9, 3.71 g (30.42 mmol) of phenylboronic acid, and 0.23 g (0.20 mmol) of Pd(PPh3)4 were dissolved in 150 ml of toluene, and 4.30 g (40.56 mmol) of Na2CO3 was put into 50 ml of distilled water, and then refluxed and agitated for 5 hours. After the reaction was finished, extraction was performed by dichloromethane, filtering was performed by silica gel, and the column was used at a ratio of Hexane:MC=7:3 (v/v) to obtain 5.81 g of 10-ethyl-3-phenyl-10H-phenanthro[9,10-b]carbazole (yield 68%).

Workup

  1. temperaturerefluxed
  2. extractionextraction
  3. filtrationfiltering

Sources & evidence

ORD record
ord-61e53b42060841ea84035bc132bbb563
Source dataset
uspto-grants-2015_04
Patent number
US09017829B2

Reaction notes

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