Benzyl Bromide → HCID 66685751, compound

To a 250 mL RB flask fitted with magnetic stirrer was charged with 30 mL of acetonitrile. To the stirred solvent were added methyl 3-(4-hydroxyphenyl)hex-4-ynoate (3.8 g, 17.4 mmol), potassium carbonate (7.2 g, 52.2 mmol). The reaction mixture was brought to 0° C., was added benzyl bromide (4.47 g, 1.5 mmol) in acetonitrile (20 mL) drop wise and stirred at room temperature for 16 h. The reaction mixture was concentrated to distill off the solvent. Water (20 mL) was added and extracted with ethyl acetate (60 mL). The organic layer was washed with water (20 mL) and saturated brine solution (20 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel column chromatography using ethyl acetate and petroleum ether as elutants to obtain product (4.2 g, yield: 78.35%).

1. customTo a 250 mL RB flask fitted with magnetic stirrer
2. customwas brought to 0° C.
3. concentrationThe reaction mixture was concentrated
4. distillationto distill off the solvent
5. additionWater (20 mL) was added
6. extractionextracted with ethyl acetate (60 mL)
7. washThe organic layer was washed with water (20 mL) and saturated brine solution (20 mL)
8. dry with materialThe organic layer was dried over anhydrous Na2SO4
9. customthe solvent was removed under reduced pressure
10. customThe crude material was purified by silica gel column chromatography

ORD record

ord-f6c1d2a9604446fcabfbef188beeefc6

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2