Cesium carbonate → 2,5-Dimethyl-4-(3,5-dimethylphenyl)indene

HRID 1372541Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.Br[C:32]1[C:40]([CH3:41])=[CH:39][CH:38]=[C:37]2[C:33]=1[CH:34]=[C:35]([CH3:42])[CH2:36]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]>[CH3:42][C:35]1[CH2:36][C:37]2[C:33]([CH:34]=1)=[C:32]([C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=1)[C:40]([CH3:41])=[CH:39][CH:38]=2

Participants

Conditions

Temperature: 80 °C

Procedure

3,5-Dimethylphenylboronic acid (2.3 g, 15 mmol), prepared as described under (e) above, cesium carbonate (4.9 g, 15 mmol), and Pd2(dba)3 (87 mg, 94 μmol) (dba=dibenzylidene acetone) were dissolved in 30 ml of 1,4-dioxane. To the resultant solution were added P(t-Bu)3 (57 μL, 280 μmol) and 4-bromo-2,5-dimethylindene (3.1 g, 15 mmol) and the reaction was stirred at 80° C. for five hours. After this time, the solvent was removed in vacuo and the residue was taken up in 100 ml of diethyl ether and filtered through a celite-packed frit to remove cesium salts. Thereafter the solvent was removed in vacuo and the residue was loaded onto a silica gel column and eluted with hexane. Yield: 2.1 g (56%).

Workup

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

Sources & evidence

ORD record: ord-7632ce5cf82a41b4a04ee9219bfbf3be
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157591B2

Reaction notes

Loading…