1,3-Dibromobenzene → 1,3-Bis(dimesitylboryl)benzene

HRID 1180357Notes

Reaction equation

HRID 1180357 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9](Br)[CH:8]=1.F[B:15]([C:25]1[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][C:26]=1[CH3:33])[C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=1[CH3:24]>CCCCCC.C1COCC1>[C:1]1([CH3:4])[CH:3]=[C:30]([CH3:29])[CH:25]=[C:26]([CH3:27])[C:2]=1[B:15]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=1[CH3:24])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([B:15]([C:25]2[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][C:26]=2[CH3:33])[C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[CH:8]=1

Participants

6

Reactant 3

HCID 79271,3-DibromobenzeneHCID 3466040Dimesitylboron fluorideHCID 178418306HCID 178418306, compound

Product 1

HCID 156850001,3-Bis(dimesitylboryl)benzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

25.9 ml (44 mmol) of a 1.7 M solution of tert-butyllithium in n-hexane was added dropwise to a well-stirred solution of 2.36 g (10 mmol) of 1,3-dibromobenzene in 200 ml of absolute THF which had been cooled to −78° C. over a period of 20 minutes at such a rate that the temperature of the reaction mixture did not exceed −65° C. The solution was stirred for another 1 hour at −78° C. and a solution of 6.44 g (24 mmol) of fluorodimesitylborane in 50 ml of absolute THF was then added dropwise over a period of 20 minutes at such a rate that the temperature of the reaction mixture did not exceed −65° C.

Workup

  1. customdid not exceed −65° C
  2. customdid not exceed −65° C.

Sources & evidence

ORD record
ord-43065a6c06fc401fa3c3b23080526364
Source dataset
uspto-grants-2007_10
Patent number
US07279603B2

Reaction notes

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