Gallium, chlorodimethyl- → o-Trifluoromethylbenzyldimethylgallium

HRID 2372542Notes

Reaction equation

HRID 2372542 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Br.C([Li])CCC.[Cl-].[CH3:19][Ga+:20][CH3:21]>CCOCC.CCCCCC.CCCCCC>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Ga:20]([CH3:21])[CH3:19]

Participants

6

Reactant 3

HCID 81329Gallium, chlorodimethyl-HCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 14692906o-Trifluoromethylbenzyldimethylgallium

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 21584099Diethylether hexaneSolvent2×

Procedure

5.25 g (22 mmol) of o-trifluoromethylbenzyl bromide in 10 ml of ether/hexane are added at -50° to a mixture of 45 ml of ether/hexane (2:1) and 14.7 ml (1.5N =22 mmol) of n-butyllithium. After stirring for 15 minutes, 2.1 g (16 mmol) of dimethylgallium chloride in 20 ml of hexane are added. Then the reaction mixture is allowed to come to room temperature, it is stirred for 24 hours, and the LiCl is filtered off and the solvent removed. After sublimation in vacuo, o-trifluoromethylbenzyldimethylgallium is obtained with a Mp. 35°-38°.

Workup

  1. customto come to room temperature
  2. stirringit is stirred for 24 hours
  3. filtrationthe LiCl is filtered off
  4. customthe solvent removed

Sources & evidence

ORD record
ord-7db2b241997c47a39394763b74c9d79f
Source dataset
uspto-grants-1992_03
Patent number
US05099044

Reaction notes

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