Chloroacetyl chloride → HCID 178468297, compound

To a suspension of ethyl 3-fluorobenzimidate hydrochloride (400 mg, 1.96 mmol) in dichloromethane (15 mL) was added triethylamine (497 mg, 684 μL, 4.91 mmol) at RT. The reaction mixture was cooled to 0-5° C. and 2-chloroacetyl chloride (333 mg, 234 μL, 2.95 mmol) was added dropwise over a period of 5 min. After 20 min the ice bath was removed and the mixture was stirred at RT for 2 h. The reaction mixture was poured into KHSO4 (10% aqueous solution, 25 mL) and extracted with dichloromethane (3×50 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give the product as light brown oil (537 mg, 1.98 mmol, 101%) which was used without further purification for the next step.

1. customAfter 20 min the ice bath was removed
2. additionThe reaction mixture was poured into KHSO4 (10% aqueous solution, 25 mL)
3. extractionextracted with dichloromethane (3×50 mL)
4. dry with materialThe combined organic layer was dried over MgSO4
5. concentrationconcentrated in vacuo

ORD record

ord-f4f3a642ca4e4c9faec9dc55c7f5208c

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772510B2