Thiophosgene → 4-Bromo-1-isothiocyanato-2-methylbenzene

Temperature

0 °C

To a solution of 4-bromo-2-methylaniline (11.0 g, 59.0 mmol) and saturated aqueous sodium hydrogen carbonate (150 mL) in tetrahydrofuran (150 mL) was added thiophosgene (4.50 mL, 59.0 mmol), and the mixture was stirred at 0° C. for 30 min. The reaction mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residual solid was collected by filtration and was washed with n-hexane to give the title compound as a brown powder (8.16 g, 35.8 mmol, 61%).

1. extractionThe reaction mixture was extracted with ethyl acetate
2. washThe combined organic layer was washed with brine
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. filtrationThe residual solid was collected by filtration
7. washwas washed with n-hexane

ORD record

ord-9f86ea1a5a9847409a33dd8005074d81

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785460B2