4-Bromotoluene → (1,1'-Biphenyl)-2-carboxylic acid, 4'-methyl-, methyl ester

HRID 1769403Notes

Reaction equation

HRID 1769403 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Ni](Cl)Cl.[Zn].N1C=CC=CC=1>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]2[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 78054-BromotolueneHCID 11776TriphenylphosphineHCID 11895Methyl 2-chlorobenzoate

Product 1

HCID 1393873(1,1'-Biphenyl)-2-carboxylic acid, 4'-methyl-, methyl ester

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24385Nickel DichlorideCatalystHCID 1049PyridineSolvent

Procedure

Into a 100 ml flask, 50 ml of dry pyridine, 4.28 g (0.025 mol) of 4-bromotoluene, 4.26 g (0.025 mol) of methyl 2-chlorobenzoate, 0.32 g (0.0025 mol) of anhydrous nickel chloride, 1.31 g (0.005 mol) of triphenylphosphine and 4.90 g (0.075 mol) of zinc powder were charged under a nitrogen atmosphere and stirred at room temperature for 30 minutes. The mixture was heated by an oil bath and reacted at 85° C. for 3 hours. The reaction solution was analyzed by gas chromatography. The results are shown in Table 1. The data confirming the structure are shown below.

Workup

  1. temperatureThe mixture was heated by an oil bath
  2. customreacted at 85° C. for 3 hours

Sources & evidence

ORD record
ord-f4a1e6d74cf4429d8189f4e706e88dc7
Source dataset
uspto-grants-1995_01
Patent number
US05380910

Reaction notes

Loading…