Chlorodimethylaluminum → HCID 16714923, compound

HRID 732266Notes

Reaction equation

HRID 732266 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].FC1C([Mg]Br)=C(F)C(F)=C(F)C=1F.[Al:18]([C:41]1C(F)=C(F)C(F)=C(F)C=1F)([C:30]1C(F)=C(F)C(F)=C(F)C=1F)[C:19]1[C:28]([F:29])=[C:26]([F:27])[C:24]([F:25])=[C:22]([F:23])[C:20]=1[F:21].[Al](Cl)(C)C.C1([Li])C(F)=C(F)C(F)=C(F)C=1F>C(OCC)C>[Al:18]([C:19]1[C:28]([F:29])=[C:26]([F:27])[C:24]([F:25])=[C:22]([F:23])[C:20]=1[F:21])([CH3:30])[CH3:41]

Participants

7

Reactant 5

HCID 79147ChlorodimethylaluminumHCID 6451240Aluminum(III) ChlorideHCID 16688462Tris(pentafluorophenyl)alumane2×HCID 178419089HCID 178419089, compoundHCID 178505971HCID 178505971, compound

Product 1

HCID 16714923HCID 16714923, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

O(CH2CH3)2} from reaction of aluminum trichloride (AlCl3) and pentafluorophenylmagnesiumbromide (BrMgC6F5) in diethyl ether is also known. However, attempts at removing the coordinated ether resulted in explosion. The synthesis of base free Al(C6F5)3 was not possible until much later. The first disclosure of a method for making base free Al(C6F5)3 was provided by researchers in 1995. This was accomplished by reaction of Me2AlCl with C6F5Li in hexanes to initially form Me2AlC6F5 which is then heated to 180° C. in vacuo to liberate AlMe3 and generate crude Al(C6F5)3. Recrystallization of the crude reaction product from THF gave the adduct THF.Al(C6F5)3 in 64% yield. This procedure is dangerous to conduct as C6F5Li is thermally unstable and the produced Al(C6F5)3 is energetic and exploded on occasion. An alternative route for the synthesis of Al(C6F5)3 involves the exchange reaction between B(C6F5)3 and trimethylaluminum which is typically conducted in an aromatic hydrocarbon (i.e., toluene). This strategy purportedly gives rise to high yields of base free Al(C6F5)3 (stable in toluene) but involves the requisite use of pyrophoric Al(CH3)3 in addition to consuming valuable B(C6F5)3.

Workup

  1. customHowever, attempts at removing the coordinated ether
  2. customresulted in explosion
  3. customwas provided by researchers in 1995

Sources & evidence

ORD record
ord-5ab2980a8bfa48a1b2a101ac3c46497d
Source dataset
uspto-grants-2009_09
Patent number
US07585991B2

Reaction notes

Loading…