Bromobenzene → Triphenylborane

HRID 370350

Reaction equation

HRID 370350 reaction equation
C[B-:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[N+](C)(C)C.C1(Br)C=CC=CC=1.[Mg].B(F)(F)F.CCOCC>C(OCC)C>[C:15]1([B:2]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 8000Boron trifluoride etherateHCID 5462224MagnesiumHCID 13498337Tetramethylammonium methyltriphenylborate

Product 1

HCID 70400Triphenylborane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In the case of the tetramethylammonium methyl triphenyl borate, concretely, its production is performed by reacting phenyl bromide with magnesium in diethyl ether to prepare a Grignard reagent, dripping it in a solution of boron trifluoride diethyl etherate in diethyl ether, and then stirring for several hours to obtain triphenylborane, followed by addition of methyllithium without isolating triphenylborane to convert it to lithium methyl triphenyl borate and by addition of tetramethylammonium bromide to effect ion exchange to obtain tetramethylammonium methyl triphenyl borate.

Sources & evidence

ORD record
ord-10910fbcd1224dc4ad56a2f324bc468b
Source dataset
uspto-grants-2000_10
Patent number
US06140537

Linked notes

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