Dichloro(diisopropylamino)borane → HCID 131734357, compound

HRID 1505833Notes

Reaction equation

HRID 1505833 reaction equation
[CH:1]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH:7]=1)=[CH:2][CH2:3][CH2:4][CH3:5].C([Li])CCC.[Cl:20][B:21](Cl)[N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24]>C(OCC)C>[Cl:20][B:21]([N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([CH:1]=[CH:2][CH2:3][CH2:4][CH3:5])=[CH:7]1

Participants

5

Reactant 3

HCID 4139105Dichloro(diisopropylamino)boraneHCID 131734356HCID 131734356, compoundHCID 178418339Butyllithium

Product 1

HCID 131734357HCID 131734357, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-74 °C

Procedure

Metallocenes MET 1, MET 3, and MET 4 were produced using suitable procedures. MET 2 was synthesized by first reacting lithiated indene with 5-bromo-1-pentene. Pure 3-(1-pentenyl) indene was obtained via vacuum distillation as a pale yellow oil. One mole of 3-(1-pentenyl) indene was added to diethyl ether and cooled to −74° C., and one mole of n-butyllithium was added. The reaction mixture was stirred at 21° C. for 3 hr, then cooled again to −74° C., followed by the addition of a diethyl ether solution of dichloro(diisopropylamino) boron, and then stirred for 12 hr while warming to 21° C. The resulting yellow slurry was centrifuged, and the bright yellow solution was poured off and solvent removed under reduced pressure. Monochloro(diisopropylamino)-3-(1-pentenyl)indenylboron was obtained as a yellow oil. One mole of monochloro(diisopropylamino)-3-(1-pentenyl)indenylboron was added to tetrahydrofuran and cooled to 0° C., followed by the addition of one mole of sodium cyclopentadiaenide, producing a yellow slurry, which was stirred at 21° C. for 12 hr. The reaction solution was centrifuged and then decanted off. Concentration under reduced atmosphere yielded the ligand shown below as a yellow oil:

Workup

  1. temperaturecooled again to −74° C.
  2. stirringstirred for 12 hr
  3. temperaturewhile warming to 21° C
  4. additionthe bright yellow solution was poured off
  5. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-829d4827df1b41429fae7e570bc33341
Source dataset
uspto-grants-2015_12
Patent number
US09217049B2

Reaction notes

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