Dichloromethane → 7-Bromo-1-chloronaphthalene

A mixture of the product from Step C (6.0 g, 30 mmol) and 6 M HCl (13.4 ml) was stirred at room temperature until a solid formed. The mixture was cooled to 0° C. and a solution of sodium nitrite (1.9 g, 30 mmol) in water (5.6 ml) was slowly added keeping the temperature below 5° C. The resulting brown slurry was stirred at 0° C. for 15 minutes and then a solution of copper(I) chloride (3.3 g, 30 mmol) in 6 M HCl (15.4 ml) was added. The mixture was stirred at 0° C. for 10 minutes, then warmed to room temperature and stirred at 60° C. for 30 minutes. After cooling to room temperature, dichloromethane was added. The mixture was filtered through diatomaceous earth and the filtrate was extracted with dichloromethane three times. The combined organic layers were washed with water and dried over magnesium sulfate to give 7-bromo-1-chloronaphthalene (2.8 g, 43%) after chromatography (100% hexanes): 1H NMR (300 MHz, DMSO-d6) δ 8.30 (d, J=1.8 Hz, 1H), 7.96-8.02 (m, 2H), 7.74-7.78 (m, 2H), 7.55 (t, J=7.8 Hz, 1H).

1. customformed
2. temperatureThe mixture was cooled to 0° C.
3. customthe temperature below 5° C
4. stirringThe resulting brown slurry was stirred at 0° C. for 15 minutes
5. stirringThe mixture was stirred at 0° C. for 10 minutes
6. temperaturewarmed to room temperature
7. stirringstirred at 60° C. for 30 minutes
8. temperatureAfter cooling to room temperature
9. filtrationThe mixture was filtered through diatomaceous earth
10. extractionthe filtrate was extracted with dichloromethane three times
11. washThe combined organic layers were washed with water
12. dry with materialdried over magnesium sulfate

ORDレコード

ord-183bb766f2ab42d4a2d42cd1166367f5

出典データセット

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08741901B2