Water → 1-Iodo-4-methyl-4-nitro-pentane

A solution of sodium iodide (17.41 g, 3.9 equiv, 116.6 mmol) in acetone (100 mL, 0.3 M) was added a flask which contained 4-methyl-4-nitropentyl methanesulfonate (6.73 g, 29.9 mmol). The flask was sealed with a septum and covered with aluminum foil and allowed to stir for 17 h. Water (20 ml) was added to the suspension and the acetone was removed by rotovap at reduced pressure. The aqueous solution was extracted with ethyl acetate (150 mL) and washed with 5% aqueous sodium thiosulfate solution (40 ml) and brine (40 ml). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to give a yellow oil (7.46 g, yield 92.0%). 1H NMR (CDCl3, 400 MHz): δ 1.60 (s, 6H), 1.78-1.82 (m, 2H), 2.01-2.04 (m, 2H), 3.14-3.18 (t, 2H). LRMS (ESI+) for C6H12INO2 (257.0); Found: 258 (MH+).

1. customThe flask was sealed with a septum
2. customthe acetone was removed by rotovap at reduced pressure
3. extractionThe aqueous solution was extracted with ethyl acetate (150 mL)
4. washwashed with 5% aqueous sodium thiosulfate solution (40 ml) and brine (40 ml)
5. dry with materialThe organic layer was dried over anhydrous MgSO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-7350c2da823145aab39b68d75d7a6c31

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278482B2