1,2-Dimethoxyethane → HCID 59795539, compound

HRID 2369758Notes

Reaction equation

HRID 2369758 reaction equation
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:38]([CH2:41]OC)OC>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.C1COCC1>[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9]([C:41]2[CH:38]=[CH:17][C:16]5[C:5](=[CH:4][CH:3]=[CH:2][CH:15]=5)[CH:6]=2)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 176470Pyrene, 1,6-Dibromo-HCID 2734375(Naphthalen-2-yl)boronic acid

Product 1

HCID 59795539HCID 59795539, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

Under an atmospheric argon gas flow, 1,6-dibromopyrene in an amount of 10.3 g (28.6 millimole), 2-naphthylboronic acid in an amount of 11.8 g (68.7 millimole), tetrakis(triphenylphosphine)palladium(0) in an amount of 0.66 g (2% by mole), sodium carbonate aqueous solution in an amount of 43 milliliter (59.4 millimole, 2M), dimethoxyethane (DME) in an amount of 100 milliliter and dried THF in an amount of 70 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 200 milliliter, and the resultant solution was stirred with heating at a temperature of 90° C. for 8 hours. After the completion of the reaction, adding 50 milliliter of water, precipitated crystal was separated by filtration and washed with the use of 50 milliliter of water and 100 milliliter of ethanol, and as a result, 13.2 g of 1,6-di(2-naphthyl)pyrene (pale yellow powder) was obtained (the yield: 99%).

Workup

  1. customequipped with a cooling pipe
  2. customAfter the completion of the reaction
  3. customprecipitated crystal
  4. customwas separated by filtration
  5. washwashed with the use of 50 milliliter of water and 100 milliliter of ethanol

Sources & evidence

ORD record
ord-e256a40bc67c4ad7b742983318493271
Source dataset
uspto-grants-2014_04
Patent number
US08709613B2

Reaction notes

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