تفاعل #80542

معادلة التفاعل

CHCl3

BBr3

(R)-8-Fluoro-3-(N-isopropyl-N-propylamino)-5-methoxy-3,4-dihydro-2H-1-benzopyran hydrochloride

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title compound

المردود 97.0%

(R)-8-Fluoro-3-(N-isopropyl-N-propylamino)-5-hydroxy-3,4-dihydro-2H -1-benzopyran

المردود 97.0%

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONadded dropwise
2. 2
   أخرىThe cooling-bath was removed and after 3 h at room temperature the reaction
3. 3
   workup.ADDITIONThe reaction was poured out onto an ice/2M NH3 solution
4. 4
   استخلاصthe mixture was extracted
5. 5
   workup.ADDITIONThe combined ether portions were treated with brine
6. 6
   تجفيفdried (Na2SO4)
7. 7
   ترشيحfiltered
8. 8
   أخرىthe solvent removed in vacuo
9. 9
   أخرىto give the crude residue

الإجراء التجريبي

(R)-8-Fluoro-3-(N-isopropyl-N-propylamino)-5-methoxy-3,4-dihydro-2H-1-benzopyran hydrochloride (1.03 g, 3.24 mmol) was dissolved in anhydrous CH2Cl2 (30 mL) and cooled to -40° C. To the solution was BBr3 (0.77 mL, 8.1 mmol), dissolved in anhydrous CH2Cl2 (5 mL), added dropwise. The cooling-bath was removed and after 3 h at room temperature the reaction was complete. The reaction was poured out onto an ice/2M NH3 solution and the mixture was extracted, twice, with diethyl ether. The combined ether portions were treated with brine, dried (Na2SO4), filtered, and the solvent removed in vacuo to give the crude residue. Chromatography on silica (eluent: 20% ethyl acetate/hexane) gave 0.84 g (97% yield) of the title compound as a clear oil [α]21D =-94.2° (C=0.1 CHCl3) GC-MS (70 eV) M=267 (26%). The hydrochloride salt was made by dissolving the pure base in diethyl ether and dropping an excess of an ethereal HCl solution. The salt was recrystallized from CHCl3 /diethyl ether/ethyl acetate to give a white solid. Mp: 220°-2° C.

المصدر