Cesium carbonate → 2,5-Dimethyl-4-(3,5-di-t-butylphenyl)indene

HRID 1372545Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.Br[C:38]1[C:46]([CH3:47])=[CH:45][CH:44]=[C:43]2[C:39]=1[CH:40]=[C:41]([CH3:48])[CH2:42]2>O1CCOCC1.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:48][C:41]1[CH2:42][C:43]2[C:39]([CH:40]=1)=[C:38]([C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=1)[C:46]([CH3:47])=[CH:45][CH:44]=2

Participants

Conditions

Temperature: 80 °C

Procedure

3,5-Di-t-butylphenylboronic acid (4.4 g, 19 mmol), prepared as described under (j) above, cesium carbonate (7.3 g, 22 mmol), and Pd2(dba)3 (0.24 g, 262 μmol) (dba=dibenzylidene acetone) were dissolved in 60 ml of 1,4-dioxane. To this solution were added P(t-Bu)3 (170 μL, 830 μmol) and 4-bromo-2,5-dimethylindene (3.1 g, 19 mmol), followed by stirring at 80° C. for five hours. After this time, the solvent was removed in vacuo and the residue was taken up in 150 ml of diethyl ether and filtered through a celite-packed frit to remove cesium salts. Then the solvent was removed in vacuo and the residue was loaded onto a silica gel column and eluted with hexane. Yield: 3.4 g (54%).

Workup

customAfter this time, the solvent was removed in vacuo
filtrationfiltered through a celite-packed frit
customto remove cesium salts
customThen the solvent was removed in vacuo
washeluted with hexane

Sources & evidence

ORD record: ord-2902f17c8e884a63bd7cf0d87a01c4cd
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157591B2

Reaction notes

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