Sodium Carbonate → HCID 11184605, compound

HRID 1473734Notes

Reaction equation

HRID 1473734 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Br:8].[CH3:9][O:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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>[Br:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([O:10][CH3:9])[CH:16]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 114141,2-DibromobenzeneHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 11184605HCID 11184605, compoundYield 69.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

20.0 g (85.52 mmol) of 1,2-dibromobenzene, 11.70 g (76.97 mmol) of 3-methoxyphenylboronic acid, 0.99 g (0.86 mmol) of Pd(PPh3)4, and 18.13 g (171.04 mmol) of sodium carbonate were put, suspended in 300 ml of toluene and 100 ml of ethanol, and refluxed and agitated for 12 hours. After the reaction was finished, extraction was performed by dichloromethane, filtering was performed by silica gel, and the column was used at a ratio of hexane:MC=4:1 (v/v) to obtain 14.12 g of 2-bromo-3′-methoxybiphenyl that was the target compound (yield 63%).

Workup

  1. extractionextraction
  2. filtrationfiltering

Sources & evidence

ORD record
ord-9673cb8fe191481888ab866a9d775424
Source dataset
uspto-grants-2015_04
Patent number
US09017829B2

Reaction notes

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