1-Naphthalen-1-ylpropan-1-one → 2-Bromo-1'-propionaphthone

Temperature

0 °C

To a solution of 1-naphthalen-1-yl-propan-l-one (37.8 g) in 1,2-dimethoxyethane (350 mL) at 0° C. was added phenyl trimethylammonium tribromide (83 g). The mixture was stirred at 0° C. for 10 minutes and then at room temperature for 24 hours. The mixture was washed with water (500 mL) and the aqueous phase was extracted with ethyl acetate (2×500 mL). The combined organics were washed with water (2×200 mL), brine (500 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford an orange gum. The gum was triturated with diethyl ether and filtered to afford 2-bromo-1-naphthalen-1-yl-propan-1-one (39.8 g, 74%) as an orange solid, 1H NMR (CDCl3): 1.95 (3H, d, J=6.6 Hz), 5.35 (1H, q, J=6.6 Hz), 7.45-7.60 (3H, m), 7.85-7.90 (2H, m), 8.0 (1H, d, J=8.1 Hz), 8.4 (1H, d, J=7.9 Hz).

1. waitat room temperature for 24 hours
2. washThe mixture was washed with water (500 mL)
3. extractionthe aqueous phase was extracted with ethyl acetate (2×500 mL)
4. washThe combined organics were washed with water (2×200 mL), brine (500 mL)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. customthe solvent removed under reduced pressure
8. customto afford an orange gum
9. customThe gum was triturated with diethyl ether
10. filtrationfiltered

ORD record

ord-17bbc17884dc4eae925ca8fc9dd03b88

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07429607B2