Ammonium Chloride → 4-(4-n-Propylphenyl)trifluorotoluene

HRID 486343

Reaction equation

HRID 486343 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[Mg].Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1.[Cl-].[NH4+]>C1COCC1.[Br-].[Zn+2].[Br-]>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 1363741-Bromo-4-propylbenzeneHCID 5462224Magnesium

Product 1

HCID 149851934-(4-n-Propylphenyl)trifluorotoluene

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

11.2 g of anhydrous zinc bromide in 25 ml of THF are added dropwise at about 0° to a Grignard solution prepared from 20 g of 4-n-propylbromobenzene and 2.4 g of magnesium turnings in 100 ml of THF. After the mixture has been stirred for 2 hours, a mixture of 22.5 g of 4-bromotrifluorotoluene, 1.5 g of [(diphenylphosphine)ferrocenyl]palladium(II) chloride and 25 ml of THF is added dropwise, and the mixture is stirred for 24 hours at room temperature and poured into 100 ml of saturated ammonium chloride solution. Customary work-up gives 4-(4-n-propylphenyl)trifluorotoluene, M.p. 97° C., Δε=14.2, viscosity η (20° C.)=6 mm2 /s.

Workup

  1. additionis added dropwise
  2. stirringthe mixture is stirred for 24 hours at room temperature

Sources & evidence

ORD record
ord-9a287455070b4912bc1db937bf0676e8
Source dataset
uspto-grants-1994_03
Patent number
US05292454

Linked notes

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