Boron tribromide → HCID 68666357, compound

Temperature

-78 °C

Boron tribromide (10.1 mL, 1.0 M in CH2Cl2, 10.1 mmol) was added dropwise to a solution of trans-5-(4-methoxy-3-methyl-phenyl)-3-(2-propenyl)-2-pyrrolidinone (1.13 g, 4.61 mmol) in 10.0 mL of CH2Cl2 at −78° C. The mixture was stirred at −78° C. for 30 min and then at 0° C. for 1 hr. The reaction was quenched by 20 mL of H2O. The mixture was poured into a mixture of ethyl ether and EtOAc (1:1, 50.0 mL) and extracted with 2.0 N of NaOH (3×30 mL). Aqueous layers were combined and acidified using 5.0 N HCl and extracted with EtOAc (3×50 mL). Organic layers were combined, dried over MgSO4, and concentrated to give 940 mg (88%) of the crude title compound as a light brown solid, which was used for next step without further purification.

1. waitat 0° C. for 1 hr
2. customThe reaction was quenched by 20 mL of H2O
3. additionThe mixture was poured into a mixture of ethyl ether and EtOAc (1:1, 50.0 mL)
4. extractionextracted with 2.0 N of NaOH (3×30 mL)
5. extractionextracted with EtOAc (3×50 mL)
6. dry with materialdried over MgSO4
7. concentrationconcentrated

ORD record

ord-54f30841678b4af1ac5ba7d8db2a4987

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07659294B2