Tris(1,1-dimethylethyl)phosphine → 2-(2,4,6-Trimethylphenyl)-1H-indene

HRID 269465Notes

Reaction equation

HRID 269465 reaction equation
[C:1]1([CH3:11])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[Mg]Br.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.Br[C:26]1[CH2:27][C:28]2[C:33]([CH:34]=1)=[CH:32][CH:31]=[CH:30][CH:29]=2>C1COCC1.[Cl-].[Na+].O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:1]1([CH3:11])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:26]1[CH2:34][C:33]2[C:28]([CH:27]=1)=[CH:29][CH:30]=[CH:31][CH:32]=2

Participants

7

Reactant 3

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 5755861H-Indene, 2-bromo-HCID 178425415HCID 178425415, compound

Product 1

HCID 598325532-(2,4,6-Trimethylphenyl)-1H-indene

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 50.0 ml (20.0 mmol) of 0.4 M mesitylmagnesium bromide in THF, 230 mg (0.40 mmol) of Pd(dba)2, 162 mg (0.80 mmol) of PtBu3, and 3.90 g (20.0 mmol) of 2-bromo-1H-indene was stirred for 48 h at ambient temperature. Then, to the resulting mixture 200 ml of brine was added. The organic layer was separated, and the aqueous layer was extracted with 3×100 ml of ether. The combined organic fractions were dried over K2CO3 and then evaporated to dryness. The product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 30 mm, l 300 mm, eluent: hexanes-dichloromethane, 20:1, vol.). Yield 3.19 g (68%) of white solid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with 3×100 ml of ether
  3. dry with materialThe combined organic fractions were dried over K2CO3
  4. customevaporated to dryness
  5. customThe product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 30 mm, l 300 mm, eluent: hexanes-dichloromethane, 20:1, vol.)

Sources & evidence

ORD record
ord-2cc2ba8275514663bbff76424205c0ef
Source dataset
uspto-grants-2008_11
Patent number
US07446216B2

Reaction notes

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