Boron tribromide → HCID 22219609, compound

HRID 1793803Notes

Reaction equation

HRID 1793803 reaction equation
C[O:2][C:3]1[C:13]2[CH2:12][CH2:11][N:10]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br.[Cl-].[NH4+]>C(Cl)Cl>[F:18][C:15]([F:16])([F:17])[C:14]([N:10]1[CH2:9][CH2:8][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([OH:2])[C:13]=2[CH2:12][CH2:11]1)=[O:19]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 22219597HCID 22219597, compound

Product 1

HCID 22219609HCID 22219609, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. stirringwith stirring over 2 hours
  2. customthe solution was partitioned between CH2Cl2 and water
  3. concentrationThe resulting mixture was concentrated
  4. concentrationThe organic layer was concentrated
  5. customto give a white solid
  6. customCrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-a88fdf25ee9e41d89c00582e0514224b
Source dataset
uspto-grants-2006_04
Patent number
US07022694B2

Reaction notes

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