1,2,4-Trimethylbenzene → HCID 59523758, compound

HRID 2179865Notes

Reaction equation

HRID 2179865 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[C:18]3[C:23]([CH:24]=[C:25]4[C:30]=2[CH:29]=[CH:28][CH:27]=[CH:26]4)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:9][CH:8]=1)(=O)=O.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.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.C(O)(C)(C)C>[C:33]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]3[C:30]4[C:25]([CH:24]=[C:23]5[C:18]=3[CH:19]=[CH:20][CH:21]=[CH:22]5)=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:9][CH:8]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

8

Reactant 4

HCID 72471,2,4-TrimethylbenzeneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 86701361HCID 86701361, compound

Product 1

HCID 59523758HCID 59523758, compoundYield 95.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

Under the nitrogen atmosphere, 4-(anthracen-9-yl)naphthalen-1-yl trifluoromethane sulfonate (30.0 g) as the sixteenth intermediate compound, phenylboronic acid (12.1 g), Pd(PPh3)4 (2.3 g), potassium phosphate (28.1 g), and a mixture solvent of pseudo cumene, t-butyl alcohol, and water (150 ml) (pseudo cumene/t-butyl alcohol/water=8/1/1 (volume ratio)) were added to a flask and refluxed for 5.5 hours. Once the heating is completed, the reaction solution was cooled to room temperature and added with water to terminate the reaction. It was then extracted with toluene. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (solvent: heptane/toluene mixture solvent). At that time, with reference to the method described in “Guideline for Experiments of Organic Chemistry (1)—Method of handling substance and separation and purification method”—published by Kagaku-Dojin Publishing Company, INC., page 94, the target compound was eluted by gradually increasing the ratio of toluene in the eluent. The crude product obtained by removing the solvent by distillation under reduced pressure was washed with heptane, followed with methanol to give 9-(4-phenylnaphthalen-1-yl)anthracene (24.1 g) as a seventeenth intermediate compound. The scheme is shown in the following “Reaction 28”.

Workup

  1. temperaturerefluxed for 5.5 hours
  2. customto terminate
  3. customthe reaction
  4. extractionIt was then extracted with toluene
  5. distillationThe solvent was distilled off under reduced pressure
  6. custompurified by silica gel column chromatography (solvent: heptane/toluene mixture solvent)
  7. customsubstance and separation and purification method”—published by Kagaku-Dojin Publishing Company, INC
  8. wash, page 94, the target compound was eluted
  9. temperatureby gradually increasing the ratio of toluene in the eluent
  10. customThe crude product obtained
  11. customby removing the solvent
  12. distillationby distillation under reduced pressure
  13. washwas washed with heptane

Sources & evidence

ORD record
ord-2ce960e58c5d40cda9f5937204f474c1
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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