Dichloroacetyl chloride → 2,2-Dichloro-N-(4-ethynylphenyl)Acetamide

4-Ethynylaniline (2.94 g, 25.1 mmol) was dissolved in anhydrous dichloromethane (20 mL) with triethylamine (4.55 mL, 32.6 mmol). The mixture was cooled in an ice-bath under nitrogen, then a solution of dichloroacetyl chloride (2.42 mL, 25.1 mmol) in anhydrous dichloromethane (20 mL) was added dropwise. After the addition was completed the ice-bath was removed and the mixture was stirred at room temperature for 12 h. The reaction mixture was then washed successively with water, 20% hydrochloric acid and saturated sodium bicarbonate solution. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound as a brown solid.

1. temperatureThe mixture was cooled in an ice-bath under nitrogen
2. additionAfter the addition
3. customwas removed
4. washThe reaction mixture was then washed successively with water, 20% hydrochloric acid and saturated sodium bicarbonate solution
5. dry with materialThe organic solution was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-428fdc1cbd7048e6a64728bd42414146

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07326790B2