Water → 4-Chloro-2-methylbiphenyl

HRID 1108517Notes

Reaction equation

HRID 1108517 reaction equation
[C:1]1([Mg]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[CH3:17].O>C1COCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:11]([CH3:17])[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 844762-Bromo-5-chlorotolueneHCID 178478979HCID 178478979, compound

Product 1

HCID 185334934-Chloro-2-methylbiphenylYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.03 mol of a phenylmagnesium chloride solution (26% by weight in THF) are added dropwise in the course of 60 minutes to a boiling solution of 1.0 mol of 2-bromo-5-chlorotoluene and 0.2 g of Pd(dppf) Cl2 *CH2Cl2 in 200 ml of THF. After stirring under reflux for eight hours (conversion >97%), the mixture is hydrolyzed with water. After purification by distillation, 4-chloro-2-methylbiphenyl is obtained as a colorless liquid in a yield of 89%.

Workup

  1. temperatureunder reflux for eight hours (conversion >97%)
  2. customAfter purification
  3. distillationby distillation

Sources & evidence

ORD record
ord-3deecb46e28e4a49ad976e7364338e4f
Source dataset
uspto-grants-2000_05
Patent number
US06066766

Reaction notes

Loading…