Sodium hydride → Ethyl 2-(Cyclopropylthio)-2,2-Difluoroacetate

An ether solution of cyclopropyl mercaptan synthesized from cyclopropyl bromide (50.0 g, 413 mmol) in accordance with the process described in literature (J. Am. Chem. Soc., 114, 3492 (1992)) was added dropwise to a solution of 60% sodium hydride (5.4 g, 135 mmol) in dimethyl sulfoxide (100 ml) under cooling with ice, and the mixture was stirred at room temperature for 10 minutes. A solution of ethyl bromodifluoroacetate (27.4 g, 135 mmol) in dimethyl sulfoxide (200 ml) was added dropwise to this solution under cooling with ice, and the resultant mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was poured into ice water to conduct extraction with ether. The solvent was distilled out of the resultant extract under reduced pressure. The resultant residue was distilled under reduced pressure to obtain the intended product (12.3 g; yield: 46.0%) as a colorless oil.

1. temperatureunder cooling with ice
2. temperatureunder cooling with ice
3. customAfter completion of the reaction
4. extractionextraction with ether
5. distillationThe solvent was distilled out of the resultant
6. extractionextract under reduced pressure
7. distillationThe resultant residue was distilled under reduced pressure
8. customto obtain the intended product (12.3 g; yield: 46.0%) as a colorless oil

ORD record

ord-668bcdfe8bd94f47a31974dc629ff4d3

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06229049B1