Triethylamine → HCID 21095788, compound

HRID 1350346Notes

Reaction equation

HRID 1350346 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([CH2:16][CH3:17])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]([P:22]([C:7]1[CH2:8][C:9]2[C:17]([CH:16]=1)=[CH:4][CH:3]=[CH:2][CH:10]=2)[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 21095788HCID 21095788, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Procedure

To 15.61 g (0.080 mol) of 2-bromo-1H-indene and 1.38 g (1.19 mmol) of Pd(PPh3)4 in 60 ml of toluene, 22.3 ml (16.19 g, 0.160 mol) of Et3N and 3.60 g (0.040 mol) of tBuPH2 were added. This mixture was refluxed for 24 hours, cooled to room temperature, and passed through short column with Silica Gel using 200 ml of toluene as eluent. The filtrate was evaporated to dryness to give oil, which after treatment with 150 ml of hot ethanol gave a gray precipitate. This precipitate was separated (G3), washed with 3×5 ml of cold ethanol and dried in vacuum. Yield 10.83 g (85%) of 15.

Workup

  1. temperatureThis mixture was refluxed for 24 hours
  2. customThe filtrate was evaporated to dryness
  3. customto give oil, which after treatment with 150 ml of hot ethanol
  4. customgave a gray precipitate
  5. customThis precipitate was separated (G3)
  6. washwashed with 3×5 ml of cold ethanol
  7. customdried in vacuum

Sources & evidence

ORD record
ord-5d6bbffd513346eead3f04b1d51dd6d0
Source dataset
uspto-grants-2007_05
Patent number
US07214746B2

Reaction notes

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