1,2-Dimethoxyethane → HCID 118292560, compound

HRID 1483886Notes

Reaction equation

HRID 1483886 reaction equation
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[C:29]([N+:30]([O-:32])=[O:31])=[C:28]2[C:33]3[C:24](=[CH:25][CH:26]=[CH:27]2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]=3[CH:16]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[C:1]1([C:15]2[C:29]([N+:30]([O-:32])=[O:31])=[C:28]3[C:33]4[C:24](=[CH:25][CH:26]=[CH:27]3)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=4[CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 118292562HCID 118292562, compound

Product 1

HCID 118292560HCID 118292560, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, 8.53 g of 1-naphthalene boronic acid, 14.7 g of 2-bromo-3-nitrofluoranthene, 1.04 g of tetrakistriphenylphosphine palladium(0), 70 mL of 1,2-dimethoxyethane, 70 mL of toluene, and 70 mL of a 2 M aqueous solution of sodium carbonate were charged in a flask, and the resultant mixture was refluxed for 8 h under heating and stirring. After cooling to room temperature, the reaction solution was extracted with toluene and then the aqueous layer was removed. The organic layer was washed with a saturated saline, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to obtain 10.4 g of 2-(1-naphthyl)-3-nitrofluoranthene.

Workup

  1. temperatureunder heating
  2. extractionthe reaction solution was extracted with toluene
  3. customthe aqueous layer was removed
  4. washThe organic layer was washed with a saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-779fc07007ab4e6a9a1585ac7840d39f
Source dataset
uspto-grants-2016_08
Patent number
US09419226B2

Reaction notes

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