Sodium Iodide → HCID 11132285, compound

HRID 1503197Notes

Reaction equation

[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][CH2:19]Cl.C(=O)([O-])[O-].[K+].[K+].[I-:27].[Na+]>CC(=O)CC>[I:27][CH2:17][CH2:18][CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A 5000 mL three-neck flask was charged with 4-hydroxybenzophenone (800.0 g; 4.036 mol), 1-bromo-3-chloropropane (832.5 g; 5.288 mol) and 2-butanone (3300 mL). Anhydrous potassium carbonate (673.6 g; 4.874 mol) was added and the reaction mixture was stirred at reflux for 100 h. Full consumption of the starting 4-hydroxybenzophenone was confirmed by HPLC. The reaction mixture was filtered, the inorganic solids were washed with 2-butanone (3×100 mL). The filtrate was evaporated, and the unreacted 1-bromo-3-chloropropane was removed by heating to 70° C. in vacuo. The residue was dissolved in acetonitrile (2000 mL) and sodium iodide (650.0 g; 4.337 mol) was added. The reaction mixture was refluxed for 8 h. The reaction mixture was filtered to give a solution of crude 4-(3-iodopropoxyl) benzophenone.

Workup

temperatureat reflux for 100 h
customconsumption of the starting 4-hydroxybenzophenone
filtrationThe reaction mixture was filtered
washthe inorganic solids were washed with 2-butanone (3×100 mL)
customThe filtrate was evaporated
customthe unreacted 1-bromo-3-chloropropane was removed
dissolutionThe residue was dissolved in acetonitrile (2000 mL)
temperatureThe reaction mixture was refluxed for 8 h
filtrationThe reaction mixture was filtered

Sources & evidence

ORD record: ord-2e7051925c5e43bd937b4db0f2d288a3
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212160B2

Reaction notes

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