Phosphorus pentachloride → HCID 59180425, compound

Temperature

77.5 °C

To a suspension of 100 (12.0 g; 35.0 mmol) in dichloroethane (300 mL) at 50° C. was added phosphorus pentachloride (11.01 g; 52.9 mmol). After addition was complete, the reaction mixture was heated at 75-80° C. overnight, cooled to 50° C., and additional phosphorus pentachloride (6.0 g; 28.8 mmol) was added. After heating at 85° C. for an additional 12 hours, the reaction mixture was again cooled to 50° C. and additional phosphorus pentachloride (2.0 g; 9.60 mmol) was added. Heating was continued at 90° C. for 4 hours, cooled to room temperature, and concentrated under reduced pressure. The resulting crude oil was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 20% v/v over 400 mL gradient elution) to give the title compound as a yellow oil (9.98 g).

1. additionAfter addition
2. temperaturecooled to 50° C.
3. temperatureAfter heating at 85° C. for an additional 12 hours
4. temperaturethe reaction mixture was again cooled to 50° C.
5. temperatureHeating
6. temperaturecooled to room temperature
7. concentrationconcentrated under reduced pressure
8. customThe resulting crude oil was purified by automated silica gel column chromatography (Biotage®)
9. washeluting with ethyl acetate/hexanes (0 to 20% v/v over 400 mL gradient elution)

ORD record

ord-11b8766a2c8d4051b8e77b0f9977e6de

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178699B2