1-Bromonaphthalene → 1,1'-Binaphthyl

HRID 467245

Reaction equation

HRID 467245 reaction equation
[C:1]1(S([O-])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Na+].Br[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.[O-2].[Ca+2]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN1CCCC1=O>[C:1]1([C:24]2[C:25]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:21]=[CH:22][CH:23]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 70011-BromonaphthaleneHCID 6850728CalciumoxideHCID 23681220Sodium naphthalene-1-sulfinate

Product 1

HCID 117891,1'-BinaphthylYield 64%

Reagents, catalysts & solvents 3

HCID 742671,2-Bis(diphenylphosphino)ethaneCatalystHCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4.28 g (20 mmol) of sodium 1-naphthalenesulfinate, 4.14 g (20 mmol) of 1-bromonaphthalene, 0.0225 g (0.1 mmol) of palladium acetate, 0.0478 g (0.12 mmol) of 1,2-bis(diphenylphosphino)ethane, 6.73 g (120 mmol) of calcium oxide and 60 ml of N-methyl-2-pyrrolidone were placed in a 100 ml round bottom flask and reacted at 150° C. in a nitrogen gas stream for 8 hours. After the completion of the reaction, the reaction mixture was analyzed by means of high performance liquid chromatography. The analysis showed that 12.8 mmol (yield 64%) of 1,1'-binaphthyl was formed in the reaction mixture solution.

Workup

  1. customreacted at 150° C. in a nitrogen gas stream for 8 hours
  2. customAfter the completion of the reaction

Sources & evidence

ORD record
ord-af30cc3459374cf5900863cea6334567
Source dataset
uspto-grants-1992_10
Patent number
US05159082

Linked notes

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