Methanol → Methyl 5-bromonaphthalene-2-carboxylate

5-Bromo-2-naphthoic acid (17.33 g, 69 mmol) and 250 mL of MeOH were combined in a flask under N2 atmosphere. Thionyl chloride (5.84 mL, 80 mmol) was added dropwise over 15 minutes at a temperature of 25-30° C. resulting in a pale yellow mixture. The mixture was heated at reflux for 3¼ hours. The resulting yellow solution was concentrated under vacuum to 137.4 g of solution and then placed in the freezer overnight. The resulting thick mixture was filtered and the solid was washed with 100 mL of cold MeOH. The solid was dried under vacuum at 50° C. to give 11.39 g of the intermediate title compound as white crystals. A second crop was filtered and washed with 100 mL of cold MeOH. The solid was dried to 1.31 g of white crystals. Yield: 69%, 2 crops.

1. customresulting in a pale yellow mixture
2. temperatureThe mixture was heated
3. temperatureat reflux for 3¼ hours
4. concentrationThe resulting yellow solution was concentrated under vacuum to 137.4 g of solution
5. customplaced in the freezer overnight
6. filtrationThe resulting thick mixture was filtered
7. washthe solid was washed with 100 mL of cold MeOH
8. customThe solid was dried under vacuum at 50° C.

ORD record

ord-e5e196a59d4a48c88be149a263260df7

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06835733B2