Bromobenzene → Triphenylborane

HRID 611958

Reaction equation

HRID 611958 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

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.

Workup

  1. additionthe reagent is added dropwise to a solution

Sources & evidence

ORD record
ord-d43520512c3c4def86ee4482ed62ddf2
Source dataset
uspto-grants-1999_12
Patent number
US06002044

Linked notes

Loading…