Isoamyl Nitrite → HCID 18434372, compound

Temperature

85 °C

A solution of isoamyl nitrite (10.05 mL, 75 mmol) in dimethyl disulfide (49.5 mL, 550 mmol) at 25° C. was slowly treated with 4-bromo-2-nitroaniline (10.85 g, 50 mmol). The reaction was exothermic with gas evolution. The resulting brown reaction mixture was heated to 80-90° C. for 2 h, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was cooled to 25° C. and then concentrated in vacuo. The resulting residue was dissolved in ethyl acetate (300 mL). The organic layer was washed successively with a 1N aqueous hydrochloric acid solution (1×300 mL) and a saturated aqueous sodium chloride solution (1×300 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 6/1 to 5/1 hexanes/ethyl acetate) afforded 4-bromo-1-methylsulfanyl-2-nitro-benzene (12.05 g, 97%) as a brown solid: EI-HRMS m/e calcd for C7H6BrNO2S (M+) 246.9372, found 246.9368.

1. temperatureThe reaction mixture was cooled to 25° C.
2. concentrationconcentrated in vacuo
3. dissolutionThe resulting residue was dissolved in ethyl acetate (300 mL)
4. washThe organic layer was washed successively with a 1N aqueous hydrochloric acid solution (1×300 mL)
5. dry with materiala saturated aqueous sodium chloride solution (1×300 mL), dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-46f5cdc867eb43498f5ce4f4620fdb22

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06369232B1