N-Formylmorpholine → HCID 90021510, compound

Temperature

-70 °C

Under Ar, a 2.5M solution of n-BuLi (6.0 mL, 15.0 mmol) was added slowly to a solution of 3-chloro-5-fluorotoluene (2.0, 13.8 mmol) in THF (20 mL) cooled in a dry ice/acetone bath at approximately −70° C. After the addition was complete, the reaction was stirred for 1 h at approximately −70° C. and a solution of N-formylmorpholine (2.3 g, 2.0 mmol) in THF (10 mL) was added dropwise. After stirring for 10 min, the reaction was allowed to warm to rt with stirring over 1 h, then cooled to −30° C. and quenched by the addition of H2O then 1M citric acid. The mixture was allowed to warm to rt with stirring and the phases were separated. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with H2O, dried with MgSO4 and concentrated to yield the title compound as an oil which solidified on standing (2.2 g, 12.8 mmol).

1. additionAfter the addition
2. stirringAfter stirring for 10 min
3. temperatureto warm to rt
4. stirringwith stirring over 1 h
5. temperaturecooled to −30° C.
6. customquenched by the addition of H2O
7. temperatureto warm to rt
8. stirringwith stirring
9. customthe phases were separated
10. extractionThe aqueous phase was extracted with EtOAc
11. washthe combined organic phases were washed with H2O
12. dry with materialdried with MgSO4
13. concentrationconcentrated

ORD record

ord-8cce8c367b72443c92b041d74c38f86c

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249160B2