1,2-Dimethoxyethane → HCID 86660651, compound

HRID 1429330Notes

Reaction equation

HRID 1429330 reaction equation
[CH:1]1[C:14]2[CH:13]=[C:12](B(O)O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](Br)=[CH:21][CH:20]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[Br:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]([C:12]2[C:11]3[C:6]([C:5]4[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=4[CH:13]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:20]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 665211,4-DibromonaphthaleneHCID 117757049-Phenanthracenylboronic acid

Product 1

HCID 86660651HCID 86660651, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

In argon atmosphere, a mixture of 19.41 g (87.4 mmol) of 9-phenanthreneboronic acid, 25.00 g (87.4 mmol) of 1,4-dibromonaphthalene, 2.02 g (1.70 mmol) of tetrakis(triphenylphosphine)palladium (0), 50 ml of dimethoxyethane, 200 ml of toluene, and 132 g of a 2 M sodium carbonate aqueous solution was stirred at a bath temperature of 85° C. for 6 h. The reaction mixture was added with water and extracted with toluene. After washing with water, the organic phase was dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel chromatography to obtain 16.02 g (yield: 55.0%) of 4-bromo-2-(9-phenanthrenyl)naphthalene.

Workup

  1. extractionextracted with toluene
  2. washAfter washing with water
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7d2fbc0c1d0443ff8fd690f6df9a1ee1
Source dataset
uspto-grants-2015_01
Patent number
US08940412B2

Reaction notes

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