1,2,4-Trimethylbenzene → HCID 86701362, compound

HRID 2179866Notes

Reaction equation

HRID 2179866 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:10]3[C:15]([C:16]([C:23]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[C:26]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[CH:25][CH:24]=4)=[C:17]4[C:22]=2[CH:21]=[CH:20][CH:19]=[CH:18]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)O1.FC(F)(F)S(O[C:46]1[CH:55]=[CH:54][C:53]2[C:48](=[CH:49][C:50]([O:56][CH3:57])=[CH:51][CH:52]=2)[CH:47]=1)(=O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C(=CC(=CC=1)C)C)C>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.O.CC(O)C>[CH3:57][O:56][C:50]1[CH:49]=[C:48]2[C:53]([CH:54]=[CH:55][C:46]([C:9]3[C:22]4[C:17]([C:16]([C:23]5[C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[C:26]([C:33]6[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=6)=[CH:25][CH:24]=5)=[C:15]5[C:10]=3[CH:11]=[CH:12][CH:13]=[CH:14]5)=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:47]2)=[CH:52][CH:51]=1

Participants

8

Reactant 4

HCID 72471,2,4-TrimethylbenzeneHCID 62657Potassium Phosphate, TribasicHCID 10892112Methanesulfonic acid, trifluoro-, 7-methoxy-2-naphthalenyl esterHCID 86701363HCID 86701363, compound

Product 1

HCID 86701362HCID 86701362, compoundYield 66.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Under the nitrogen atmosphere, 4,4,5,5-tetramethyl-2-(10-(4-phenylnaphthalen-1-yl)anthracen-9-yl)-1,3,2-dioxaborolane (23.0 g) as the nineteenth intermediate compound, 7-methoxynaphthalen-2-yl trifluoromethane sulfonate (18.0 g), Pd(PPh3)4 (1.6 g), potassium phosphate (19.3 g), and a mixture solvent (125 ml) of pseudo cumene, IPA, and water (pseudo cumene/IPA/water=20/4/1 (volume ratio)) were added to a flask and refluxed for 5 hours. Once the heating is completed, liquid separation was performed by adding water and toluene. The solvent was distilled off under reduced pressure and the resulting solid was purified by silica gel column chromatography (solvent: heptane/toluene=1/1). The obtained crude product was washed further with methanol to give 9-(7-methoxynaphthalen-2-yl)-10-(4-phenylnaphthalen-1-yl)anthracene (16.3 g) as a twentieth intermediate compound. The scheme is shown in the following “Reaction 32”.

Workup

  1. temperaturerefluxed for 5 hours
  2. customliquid separation
  3. additionby adding water and toluene
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting solid was purified by silica gel column chromatography (solvent: heptane/toluene=1/1)
  6. customThe obtained crude product
  7. washwas washed further with methanol

Sources & evidence

ORD record
ord-ad0e26bb363b4a2b948047515afc3827
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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