4,4'-Dibromobiphenyl → 4,4'-Bis(dimesitylboryl)biphenyl

HRID 1180358Notes

Reaction equation

HRID 1180358 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.F[B:21]([C:31]1[C:36]([CH3:37])=[CH:35][C:34]([CH3:38])=[CH:33][C:32]=1[CH3:39])[C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=1[CH3:30]>CCCCCC.C1COCC1>[C:1]1([CH3:4])[CH:3]=[C:36]([CH3:35])[CH:31]=[C:32]([CH3:33])[C:2]=1[B:21]([C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=1[CH3:30])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([B:21]([C:31]3[C:36]([CH3:37])=[CH:35][C:34]([CH3:38])=[CH:33][C:32]=3[CH3:39])[C:22]3[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[CH3:30])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 71104,4'-DibromobiphenylHCID 3466040Dimesitylboron fluorideHCID 178418306HCID 178418306, compound

Product 1

HCID 220570624,4'-Bis(dimesitylboryl)biphenyl

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

28.5 ml (48 mmol) of a 1.7 M solution of tert-butyllithium in n-hexane was added dropwise to a well-stirred suspension of 3.12 g (10 mmol) of 4,4′-dibromobiphenyl 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 suspension was stirred at −78° C. for another 1 hour and a solution of 6.44 g (24 mmol) of fluorodimesitylborane in 100 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-72c1c1ca12644fdfbbefc039da2c9f0e
Source dataset
uspto-grants-2007_10
Patent number
US07279603B2

Reaction notes

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