Water → 3-Bromo-4-(phenylmethoxy)-benzonitrile

온도

48 °C

To a solution of 3-bromo-4-hydroxybenzonitrile (60 g, 303 mmol) in acetone (600 mL) under nitrogen, potassium carbonate (62.8 g, 455 mmol) was added followed by potassium iodide (0.503 g, 3.03 mmol). To the mixture benzyl chloride (49.3 mL, 424 mmol) was added dropwise and the mixture was heated at 50° C. (48° C. internal temp) for 16 h. Reaction mixture was cooled down to room temperature, taken up with water (500 mL)/Et2O (1 L). Phases were separated and the aqueous phase back extracted with Et2O (2×500 mL). Combined organics were washed with NaHCO3 saturated solution (400 mL), then with 1M HCl solution (400 mL) and brine. Crude solution was then dried over Na2SO4 and evaporated under reduced pressure to give crude material (110 g) as brown solid that was triturated with c-hex (500 mL) for 30 min. The solid was collected by filtration and washed with c-hex/EtOAc 9/1 (200 mL). Evaporation of residual solvents under high vacuum afforded title material (75.5 g; 261 mmol; 86%) as pale brown solid.

1. customReaction mixture
2. temperaturewas cooled down to room temperature
3. customPhases were separated
4. extractionthe aqueous phase back extracted with Et2O (2×500 mL)
5. washCombined organics were washed with NaHCO3 saturated solution (400 mL)
6. dry with materialCrude solution was then dried over Na2SO4
7. customevaporated under reduced pressure
8. customto give crude material (110 g) as brown solid that
9. customwas triturated with c-hex (500 mL) for 30 min
10. filtrationThe solid was collected by filtration
11. washwashed with c-hex/EtOAc 9/1 (200 mL)
12. customEvaporation of residual solvents under high vacuum

ORD 기록

ord-87caa3422da245ebb4b84704493a3458

출처 데이터셋

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08299257B2