Hydrochloric Acid → 5-Bromo-3-(dichloromethyl)-2-nitrothiophene

Temperature

-78 °C

A solution of 2-bromo-5-nitrothiophene (29 g, 139 mmol) and chloroform (12.37 mL, 153 mmol) in DMF (110 mL) was added dropwise to a solution of potassium tert-butoxide (62.6 g, 558 mmol) in THF (225 mL)/DMF (180 mL). The internal temperature was monitored and maintained at <−60° C. during the addition. Upon complete addition, the reaction was stirred at −78° C. for 30 minutes. 2 N HCl was added and the products were extracted into EtOAc (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by flash silica gel column chromatography (0-10% EtOAc-hexanes) gave the title compound as a brown oil.

1. temperaturemaintained at <−60° C. during the addition
2. additionUpon complete addition
3. extractionthe products were extracted into EtOAc (3×)
4. washThe combined organic extracts were washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customPurification of the residue by flash silica gel column chromatography (0-10% EtOAc-hexanes)

ORD record

ord-cab979c802244a5880ba18a869649520

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420695B2