Cesium carbonate → Bis(2-hexyl) 2,3,5,6-tetraiodoterephthalate

HRID 375031Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:8]([CH2:10][CH2:11][CH2:12][CH3:13])[CH3:9].[I:14][C:15]1[C:23]([I:24])=[C:22]([C:25]([O-:27])=[O:26])[C:21]([I:28])=[C:20]([I:29])[C:16]=1[C:17]([O-:19])=[O:18]>CN(C=O)C>[I:14][C:15]1[C:23]([I:24])=[C:22]([C:25]([O:27][CH:8]([CH2:10][CH2:11][CH2:12][CH3:13])[CH3:9])=[O:26])[C:21]([I:28])=[C:20]([I:29])[C:16]=1[C:17]([O:19][CH:8]([CH2:10][CH2:11][CH2:12][CH3:13])[CH3:9])=[O:18]

Participants

Conditions

Temperature: 76 °C

Procedure

Cesium carbonate (1.63 g, 5.0 mmol) and 2-bromohexane (2.0 ml, 16 mmol) were added to a flask containing a stirred mixture of 2,3,5,6-tetraiodoterephthalate acid (1.4 g, 2.0 mmol) and dry DMF (20 ml). The reaction flask was immersed in an oil bath which was warmed to 76° C. over a period of 0.5 hr. After stirring under an atmosphere of N2 for 22 hrs, the reaction was allowed to cool, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into EtOAc (200 ml), washed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:19; Et2O: hexanes) provided bis(2-hexyl) 2,3,5,6-tetraiodoterephthalate (0.52 g, 44%) as a light yellow solid. Mp 114°-115° C.

Workup

additioncontaining
customThe reaction flask was immersed in an oil bath
temperatureto cool
filtrationfiltered through a pad of celite
customevaporated in vacuo
washwashed with saturated aqueous sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml)
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-3cb267d372d54d5fb449dc2460d7478e
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05484585

Reaction notes

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