Triethylamine → HCID 21095787, compound

HRID 1350345Notes

Reaction equation

HRID 1350345 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.CCN(CC)CC.[C:18]([PH2:22])([CH3:21])([CH3:20])[CH3:19]>C1(C)C=CC=CC=1.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>[C:18]([PH:22][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 123165tert-ButylphosphineHCID 5755861H-Indene, 2-bromo-

Product 1

HCID 21095787HCID 21095787, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To 9.61 g (0.049 mol) of 2-bromo-1H-indene and 1.13 g (0.98 mmol) of Pd(PPh3)4 in 25 ml of toluene, 7.5 ml (5.45 g, 0.054 mol) of Et3N and 4.88 g (0.054 mol) of tBuPH2 were added. This mixture was refluxed for 14 hours, cooled to room temperature, and filtered through glass frit (G3) to separate out compound 15. The filtrate was evaporated to dryness. The crude product was distilled in vacuum (108–110° C./3 mm). Yield 3.07 g (31%) of crystalline solid of 14.

Workup

  1. temperatureThis mixture was refluxed for 14 hours
  2. filtrationfiltered through glass frit (G3)
  3. customto separate out compound 15
  4. customThe filtrate was evaporated to dryness
  5. distillationThe crude product was distilled in vacuum (108–110° C./3 mm)

Sources & evidence

ORD record
ord-4f9e706e5c0943cc9879954867cb10a5
Source dataset
uspto-grants-2007_05
Patent number
US07214746B2

Reaction notes

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