Triphenylborane → Lithium methyltriphenylborate

HRID 611959Notes

Reaction equation

HRID 611959 reaction equation
[C:1]1([B:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][Li:21]>[Br-].C[N+](C)(C)C>[CH3:20][B-:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[Li+:21]

Participants

4

Reactant 2

HCID 70400TriphenylboraneHCID 178418348HCID 178418348, compound

Product 1

HCID 131721491Lithium methyltriphenylborate

Reagents, catalysts & solvents 1

HCID 66137Tetramethylammonium bromideCatalyst

Procedure

More specifically, in the case of the tetramethylammonium methyltriphenylborate, phenyl bromide is reacted with metallic magnesium in diethyl ether to prepare a Grignard reagent, the reagent is added dropwise to a solution containing boron trifluoride diethyl etherate dissolved in diethyl ether, the mixed solution is stirred for several hours to obtain triphenylborane, the triphenylborane obtained is added to methyllithium without passing through isolation to form lithium methyltriphenylborate, and tetramethylammonium bromide is added thereto to effect ion exchanging, as a result, tetramethylammonium methyltriphenylborate is obtained.

Sources & evidence

ORD record
ord-9014111a7f324e85ac029fa505e1a305
Source dataset
uspto-grants-1999_12
Patent number
US06002044

Reaction notes

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