1H-Indene, 2-bromo- → HCID 23148929, compound

HRID 1925195Notes

Reaction equation

HRID 1925195 reaction equation
Br[C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[Mg].C1C2C(=CC=CC=2)C=C1.Br[Mg].[CH2:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]1[B:32]([N:34]([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36])Cl>O1CCCC1>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:2]1[B:32]([C:24]1[CH2:25][C:26]2[C:31]([CH:23]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:34]([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:36])[CH3:37]

Participants

6

Reactant 4

HCID 5755861H-Indene, 2-bromo-HCID 5462224MagnesiumHCID 23148931HCID 23148931, compound2×HCID 178419821HCID 178419821, compound

Product 1

HCID 23148929HCID 23148929, compoundYield 121%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a stream of nitrogen, 3.1 g (15.9 mmol) of 2-bromoindene and 1.6 g of magnesium were caused to react with each other in 50 ml of tetrahydrofuran, whereby a reaction solution containing bromomagnesium indene was obtained. The reaction solution was added dropwise to a solution prepared by dissolving 4.11 g (15.7 mmol) of (2-indenyl)(diisopropylamino)chloroborane synthesized in the above section (1) in 30 ml of tetrahydrofuran at 0° C. After the mixture had been stirred at room temperature for 4 hours, the solvent was removed by distillation, and the remainder was extracted twice with 40 ml of hexane and 10 ml of dichloromethane, whereby 6.47 g (19.0 mmol) of bis(2-indenyl)(diisopropylamino)borane as a pale yellow solid were obtained.

Workup

  1. customwas obtained
  2. additionThe reaction solution was added dropwise to a solution
  3. customprepared
  4. customthe solvent was removed by distillation
  5. extractionthe remainder was extracted twice with 40 ml of hexane and 10 ml of dichloromethane

Sources & evidence

ORD record
ord-848482bff6324218914918521d08c64d
Source dataset
uspto-grants-2012_05
Patent number
US08178635B2

Reaction notes

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