反应 #1880985

反应方程式

6-Methoxy-3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Boron tribromide

ammonium chloride

→

title compound

收率 91.4%

3-(Trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-6-ol

收率 91.4%

溶剂

CH2Cl2

CH2Cl2

反应条件

后处理

1. 1
   workup.STIRRINGwith stirring over 2 hours
2. 2
   其他the solution was partitioned between CH2Cl2 and water
3. 3
   浓缩The resulting mixture was concentrated
4. 4
   浓缩The organic layer was concentrated
5. 5
   其他to give a white solid
6. 6
   其他Crystallization from EtOAc/hexane

实验过程

6-Methoxy-3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine (11.5 g, 42.0 mmol) was dissolved in CH2Cl2 (200 mL) and cooled to 0° C. under nitrogen. Boron tribromide (10.0 mL, 0.105 mol) was added via syringe, and the solution was stirred at room temperature for 16 hours. Saturated ammonium chloride was added slowly with stirring over 2 hours. Additional CH2Cl2 was added and the solution was partitioned between CH2Cl2 and water. The resulting mixture was concentrated and repartitioned between ethyl acetate and H2O. The organic layer was concentrated to give a white solid. Crystallization from EtOAc/hexane gave 9.95 g (91%) of the title compound as a white crystalline solid: mp 183–186° C.; 1H NMR (400 MHz, DMSO-d6) δ 6.93 (dt, J=2, 8 Hz, 1 H), 6.71 (dd, J=4, 8 Hz, 1 H), 6.61 (t, J=6 Hz, 1 H), 3.68–3.60 (m, 4 H), 3.00–2.88 (m, 4 H); IR (diffuse reflectance) 3311, 1671, 1466, 1375, 1337, 1313, 1277, 1217, 1199, 1175, 1160, 1147, 949, 785, 739 cm31 1; MS (EI) m/z 259 (M+); Anal. Calcd for C12H12F3N O2: C, 55.60; H, 4.67; N, 5.40; F, 21.99. Found: C, 55.24; H, 4.75; N, 5.36.

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