1,2-Dimethoxyethane → 2-(6-Bromonaphthalen-2-yl)dibenzofuran

HRID 1429337Notes

Reaction equation

HRID 1429337 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1B(O)O.[Br:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23](Br)[CH:24]=2)[CH:19]=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>[Br:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([C:2]1[CH:3]=[CH:4][C:5]3[O:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=1)[CH:22]=[CH:21]2

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 6405912,6-DibromonaphthaleneHCID 12032376Dibenzo(b,d)furan-2-ylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 585690572-(6-Bromonaphthalen-2-yl)dibenzofuranYield 40.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

In argon atmosphere, a mixture of 18.53 g (87.4 mmol) of 2-dibenzofuranboronic acid, 25.00 g (87.4 mmol) of 2,6-dibromonaphthalene, 5.05 g (4.40 mmol) of tetrakis(triphenylphosphine)palladium (0), 300 ml of dimethoxyethane, and 132 g of a 2 M sodium carbonate aqueous solution was stirred at a bath temperature of 85° C. for 7 h. The reaction mixture was added with water and extracted with toluene. After washing with water, the organic phase was dried over magnesium sulfate. Then, the solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel chromatography to obtain 13.20 g (yield: 38%) of 2-(6-bromonaphthalene-2-yl)dibenzofuran.

Workup

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

Sources & evidence

ORD record
ord-cc5c485afd43429288c31c60f9ca9747
Source dataset
uspto-grants-2015_01
Patent number
US08940412B2

Reaction notes

Loading…