Benzyl chloroformate → HCID 58687102, compound

To a light brown solution of 3-amino-2-fluorobenzonitrile (2.7141 g, 19.94 mmol) and potassium carbonate (4.13 g, 29.9 mmol) in THF (166 mL) was syringed benzyl carbonochloridate (4.49 mL, 29.9 mmol) under nitrogen, and the reaction was stirred overnight. The insoluble material was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc (200 mL) and washed with 1 N aqueous HCl (50 mL), water (50 mL) and brine (50 mL), successively. The organic solution was dried over MgSO4 and concentrated in vacuo to give crude product which was stirred in hexanes (75 mL) for 1 hr. The insoluble material was filtered and washed with hexanes to give the desired product (4.4541 g, 16.48 mmol, 83% yield) as a light tan solid.

1. filtrationThe insoluble material was filtered
2. concentrationthe filtrate was concentrated in vacuo
3. dissolutionThe residue was dissolved in EtOAc (200 mL)
4. washwashed with 1 N aqueous HCl (50 mL), water (50 mL) and brine (50 mL)
5. dry with materialThe organic solution was dried over MgSO4
6. concentrationconcentrated in vacuo
7. customto give crude product which
8. filtrationThe insoluble material was filtered
9. washwashed with hexanes

ORD record

ord-35552c18e5144906aa03d1210beab117

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685969B2