Dabco → HCID 86615600, compound

HRID 2219819Notes

Reaction equation

HRID 2219819 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1Br.N12[CH2:16][CH2:15]N(CC1)CC2.[CH:17]12[PH:25][CH:21]([CH2:22][CH2:23][CH2:24]1)[CH2:20][CH2:19][CH2:18]2.Br.N12[CH2:34][CH2:33]N(CC1)CC2>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C(C)=CC=CC=1>[C:21]12([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:16]34[PH:25][CH:21]([CH2:33][CH2:34][CH2:15]3)[CH2:20][CH2:19][CH2:18]4)[PH:25][CH:17]([CH2:24][CH2:23][CH2:22]1)[CH2:18][CH2:19][CH2:20]2

Participants

7

Reactant 4

HCID 9237DabcoHCID 114141,2-DibromobenzeneHCID 1171719-Phosphabicyclo[3.3.1]nonaneHCID 19608301HCID 19608301, compound

Product 1

HCID 86615600HCID 86615600, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

A 300 ml Schlenk vessel under nitrogen atmosphere is charged with 9.44 g (40 mmol) of 1,2-dibromobenzene, 22.4 g (200 mmol) of 1,4-diazabicyclo[2,2,2]octane, 13 g (91 mmol) of 9-phosphabicyclo[3.3.1]nonane, 2.32 g (2 mmol) of tetrakis(triphenylphosphine)palladium(0) and 150 ml of xylene (solvent). The mixture is stirred overnight at 140° C., during which period a precipitate of 1,4-diazabicyclo[2,2,2]octane hydrogenbromide is formed. After cooling to 100° C. the mixture is filtered hot. Upon cooling of the xylene solution, crystals of 1,2-bis-([3.3.1]-9-phosphabicyclononane) benzene are formed. The liquid is decanted, and the product recrystallized from 100 ml of hot toluene. 1,2-bis(9-phosphabicyclo[3.3.1]nonyl) benzene is obtained in a yield of 7.1 g (20 mmol, 50%), pure according to 31p and 1H NMR, 31P NMR (CD2Cl2): −16.6 ppm 1H NMR (CD2Cl2): 7.15 ppm (m, 2H), 7.10 ppm (m, 2H), 2.63 ppm (s, 4H), 12-2.2 ppm (m, 24H)

Workup

  1. customis formed
  2. filtrationis filtered hot
  3. temperatureUpon cooling of the xylene solution, crystals of 1,2-bis-([3.3.1]-9-phosphabicyclononane) benzene
  4. customare formed
  5. customThe liquid is decanted
  6. customthe product recrystallized from 100 ml of hot toluene

Sources & evidence

ORD record
ord-5f9e8b0efd9f4ad8a77573751fc1baf7
Source dataset
uspto-grants-2008_08
Patent number
US07414155B2

Reaction notes

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