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0 °C

Sodium azide 1.1 g (16.92 mmol) was added to a mixture of 6.0 mL of chloroform and 1.1 mL of water at 0° C. Concentrated sulfuric acid (0.44 mL) was added dropwise and the mixture stirred at 0° C. for two hours then filtered. The chloroform layer containing hydrazoic acid was added to a solution of 1.3 g (7.92 mmol) of 6-fluoro-1-tetralone (prepared by the method of Allinger and Jones, J. Org. Chem., 27, 70-76 (1962)) in 4.8 mL of chloroform. Additional sulfuric acid (2.16 mL) was added dropwise with stirring while maintaining the temperature below 40° C. The mixture was stirred at 40° C. for two hours then at room temperature for 16 hours. The mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was added to ice; the resulting precipitate was extracted with methylene chloride (5×). The combined extracts were washed with brine, dried over magnesium sulfate and filtered through a silica plug. Solvents were removed under vacuum to afford 162 mg (0.92 mmol,11%) of the product. 1H NMR (300 MHz, CDCl3): 2.21 (m,2H), 2.32 (t,7 Hz,2H), 2.77 (t,7 Hz,2H), 6.93 (m,3H), 7.8 (br s,1H). FAB-MS: calculated for C10H10FNO 179; found 180 (M+H,100%).

1. filtrationthen filtered
2. additionThe chloroform layer containing hydrazoic acid
3. customprepared by the method of Allinger and Jones, J
4. stirringwith stirring
5. temperaturewhile maintaining the temperature below 40° C
6. stirringThe mixture was stirred at 40° C. for two hours
7. waitat room temperature for 16 hours
8. customThe mixture was transferred to a separatory funnel
9. customthe layers were separated
10. additionThe aqueous layer was added to ice
11. extractionthe resulting precipitate was extracted with methylene chloride (5×)
12. washThe combined extracts were washed with brine
13. dry with materialdried over magnesium sulfate
14. filtrationfiltered through a silica plug
15. customSolvents were removed under vacuum