Reaktion #1772008

Reaktionsgleichung

2-(4′-Amino-3′-iodophenyl)-6-methoxy benzothiazole

BBr3

→

2-(3′-iodo-4′-aminophenyl)-6-hydroxybenzothiazole

Ausbeute 61.1%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter the reaction was quenched with water
2. 2
   ExtraktionThe aqueous layer was extracted with ethyl acetate (3×3 mL)
3. 3
   Trocknendried over MgSO4
4. 4
   SonstigeThe solvent was then evaporated under reduced pressure
5. 5
   Sonstigethe residue was purified by preparative TLC (Hexanes:ethyl acetate=7:3)

Vorschrift

To a solution of 2-(4′-Amino-3′-iodophenyl)-6-methoxy benzothiazole (5) (8.0 mg, 0.02 mmol) in CH2Cl2 (2.0 mL) was injected 1 M BBr3 solution in CH2Cl2 (0.20 ml, 0.20 mmol) under N2 atmosphere. The reaction mixture was stirred at room temperature for 18 hrs. After the reaction was quenched with water, the mixture was neutralized with NaHCO3. The aqueous layer was extracted with ethyl acetate (3×3 mL). The organic layers were combined and dried over MgSO4. The solvent was then evaporated under reduced pressure and the residue was purified by preparative TLC (Hexanes:ethyl acetate=7:3) to give 2-(3′-iodo-4′-aminophenyl)-6-hydroxybenzothiazole (4.5 mg, 58%) as a brown solid. 1HNMR (300 MHz, acetone-d6) δ (ppm): 8.69 (s, 1H), 8.34 (d, J=2.0 Hz, 1H), 7.77 (dd, J1=2.0 Hz, J2=8.4 Hz, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.40 (d, J=2.4 Hz, 1H), 7.02 (dd, J1=2.5 Hz, J2=8.8 Hz, 1H), 6.94 (d, J=8.5 Hz, 1H), 5.47 (br., 2H). HRMS m/z 367.9483 (M+calcd for C13H9N2OSI 367.9480).

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