4,4'-Dibromobiphenyl → 1-Bromonaphthalene

HRID 1198645Notes

Reaction equation

HRID 1198645 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=CC=2)=[CH:4][CH:3]=1.[Mg].[Cl-].[Cl-].C(C1C=C(C(C)(C)C)C=CC=1OP(O)O)(C)(C)C>O1CCCC1.O1CCCC1.CCCCCCC>[Br:14][C:11]1[C:4]2[C:5](=[CH:6][CH:7]=[CH:2][CH:3]=2)[CH:8]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 71104,4'-DibromobiphenylHCID 5462224MagnesiumHCID 131718319HCID 131718319, compound

Product 1

HCID 70011-BromonaphthaleneYield 200%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21263495Tetrahydrofuran heptaneSolvent

Procedure

4,4'-Biphenylene-bis- (1-naphthyl-phosphinous acid 2,4-di-tert-butylphenyl ester): in deviation from the general instructions, 200 mmol (=62.4 g) of 4,4'-dibromobiphenyl were subjected to a Grignard reaction with 600 mmol (=14.6 g) of magnesium filings in 600 ml of tetrahydrofuran under the action of ultrasound (40 kHz), and the product was then reacted with 400 mmol (=122.9 g) of phosphorous acid 2,4-di-tert-butylphenyl ester-dichloride in 700 ml of tetrahydrofuran/heptane=1/6. The Grignard reagent obtained from 82.8 g (400 mmol) of 1-bromonaphthalene was added dropwise to the resulting suspension. The mixture was filtered and the filtrate was concentrated in vacuo to give 175 g of yellow resin having a content of 76% of the above compound 31P-NMR: δ(CDCl103.7 ppm]. Pale yellow crystals of melting point 255° C. crystallized from acetone.

Sources & evidence

ORD record
ord-eb08d97226d24fd2b8433b8b71d62475
Source dataset
uspto-grants-1994_01
Patent number
US05281640

Reaction notes

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