PREPARATION OF IODOTETRALONE

Notes:

[1] Transfer to large multi-neck flask. Amount of cold H₂O: 0.5 - 1.0 ml/1mmol SM

[2] Temp.: 0 -5 ^oC during addition

[3] Temp.: 0 -5 ^oC during addition. ¯ black appear

[4] Brownish vapor(I₂) . Black gum appear. Small work up: TLC

[5] TLC w/ 5% EtOAc/Hex. Product polar < SM

38318-050

1. Dissolve Aminotetralone in HCl (conc.). Add iced-cold water [1].

2. Cold to 0 ^oC. Add dropwise NaNO₂/water [2]

3. Stir at 0 ^oC for 30 min.. Add dropwise KI/water [3]

4. Warm to R.T. and let standing (no stirring) for 30 min [4]

5. Dilute w/EtOAc. Stir for 15 min

6. Extract aqueous layer w/EtOAc

7. Wash w/ 20% aq. Na₂S₂O₃ then brine

8. Dry organic layers w/MgSO₄. Filter [5].

9. Concentrate on Rotovac ® Dark brown oil

10. Chromatograph w/ 2% ® 5% EtOAc/Hex

11. NMR w/ CDCl₃. Yield 65% as light yellow solid