1,2,4-Trimethylbenzene → HCID 86701359, compound

HRID 2179863Notes

Reaction equation

HRID 2179863 reaction equation
Br[C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH2:16]([O:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](B(O)O)=[CH:21][CH:20]=1)[CH3:17].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C(=CC(=CC=1)C)C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(O)(C)(C)C>[CH2:16]([O:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([C:2]2[C:15]3[C:10]([CH:9]=[C:8]4[C:3]=2[CH:4]=[CH:5][CH:6]=[CH:7]4)=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:21][CH:20]=1)[CH3:17]

Participants

8

Reactant 4

HCID 72471,2,4-TrimethylbenzeneHCID 62657Potassium Phosphate, TribasicHCID 740629-BromoanthraceneHCID 68010159HCID 68010159, compound

Product 1

HCID 86701359HCID 86701359, compoundYield 85.7%

Reagents, catalysts & solvents 3

HCID 75806TricyclohexylphosphineCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 6386tert-ButanolSolvent

Procedure

9-bromoanthracene (75.0 g), (4-ethoxynaphthalen-1-yl)boronic acid (78.0 g), Pd(dba)2 (5.0 g), tricyclohexyl phosphine (4.9 g), potassium phosphate (124.0 g), and a mixture solvent (440 ml) of pseudo cumene and t-butyl alcohol (pseudo cumene/t-butyl alcohol=10/1 (volume ratio)) were added to a flask and refluxed for 8 hours. The reaction solution was cooled to room temperature and the precipitated solid were collected by suction filtration. The obtained solid was washed with aqueous solution of EDTA.4Na, water, and methanol in order. It was then dissolved in heated chlorobenzene and then subjected to suction filtration by using a Kiriyama funnel layered with silica gel. The crude product obtained by removing filtrate by distillation under reduced pressure was washed with heptane while being heated to give 9-(4-ethoxynaphthalen-1-yl)anthracene (87.1 g) as a fourteenth intermediate compound. The scheme is shown in the following “Reaction 25”.

Workup

  1. temperaturerefluxed for 8 hours
  2. filtrationthe precipitated solid were collected by suction filtration
  3. washThe obtained solid was washed with aqueous solution of EDTA
  4. dissolutionIt was then dissolved in heated chlorobenzene
  5. filtrationsubjected to suction filtration
  6. customThe crude product obtained
  7. customby removing filtrate
  8. distillationby distillation under reduced pressure
  9. washwas washed with heptane
  10. temperaturewhile being heated

Sources & evidence

ORD record
ord-3b433340bd8048448e6661e6424fc48d
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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