Water → 1,4-Bis(dimesitylboryl)benzene

HRID 1106388Notes

Reaction equation

HRID 1106388 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].Br[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=1[CH3:15].Br[B:17](Br)[C:18]1[CH:23]=[CH:22][C:21]([B:24](Br)Br)=[CH:20][CH:19]=1.O>CCCCC.CCCCCC>[C:1]1([CH3:4])[CH:3]=[C:12]([CH3:11])[CH:7]=[C:8]([CH3:9])[C:2]=1[B:17]([C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=1[CH3:15])[C:18]1[CH:23]=[CH:22][C:21]([B:24]([C:7]2[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[CH3:15])[C:7]2[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[CH3:15])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 684732-BromomesityleneHCID 13678298(1,4-Phenylene)bis(dibromoborane)HCID 178418306HCID 178418306, compound

Product 1

HCID 220570631,4-Bis(dimesitylboryl)benzeneYield 52.2%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8058HexaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2 equivalents (0.08 mol) of t-butyllithium in pentane are added over the course of one hour at 0° C. to a solution of 8 g (0.04 mol) of bromomesitylene in 100 ml of hexane. The mixture is refluxed for 3 hours. After cooling to 0° C., a solution of 4.17 g (0.01 mol) of 1,4-bis(dibromoboryl)benzene in 80 ml of hexan is added to the mixture and the batch is refluxed overnight. The thick suspension produced is poured into 200 ml of water and subjected twice to extraction with 50 ml of hexane. The combined organic phases are dried over magnesium sulphate, filtered and concentrated. A yellow solid is formed which is recrystallized from hexane, giving 3.0 g (52% of theory) of 1,4-bis(dimesitylboryl)benzene.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. temperaturethe batch is refluxed overnight
  3. customThe thick suspension produced
  4. extractionsubjected twice to extraction with 50 ml of hexane
  5. dry with materialThe combined organic phases are dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customA yellow solid is formed which
  9. customis recrystallized from hexane

Sources & evidence

ORD record
ord-e9da55d4bd834d4e8e56f48182e70553
Source dataset
uspto-grants-2000_05
Patent number
US06057078

Reaction notes

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