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 in vacuo to 137.4 g of solution 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 in vacuo at 50° C. to give 11.39 g of 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 in vacuo to 137.4 g of solution
5. customthen placed 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 in vacuo at 50° C.

ORD record

ord-758b869c041444169d91d29332307d28

Source dataset

uspto-grants-2005_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06844344B2