1,2-Dimethoxyethane → 7-Bromo-2-(9-phenanthrenyl)naphthalene

HRID 1429328Notes

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[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][C:23](Br)=[CH:24][CH:25]=2)[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[CH:20]=[C:21]2[C:26]([CH:25]=[CH:24][C:23]([C:12]3[C:11]4[C:6]([C:5]5[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=5[CH:13]=3)=[CH:7][CH:8]=[CH:9][CH:10]=4)=[CH:22]2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 85 °C

Procedure

In argon atmosphere, a mixture of 18.64 g (83.9 mmol) of 9-phenanthreneboronic acid, 30.00 g (104.9 mmol) of 2,7-dibromonaphthalene, 4.85 g (4.2 mmol) of tetrakis(triphenylphosphine)palladium (0), 200 ml of dimethoxyethane, 200 ml of toluene, and 106 ml of a 2 M sodium carbonate 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 toluene was removed by distillation under reduced pressure, and the residue was purified by silica gel chromatography to obtain 12.46 g (yield: 31.0%) of 7-bromo-2-(9-phenanthrenyl)naphthalene.

Workup

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

Sources & evidence

ORD record: ord-036d58eace664723946406ef9fdfad22
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940412B2

Reaction notes

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