Boron tribromide → HCID 22413361, compound

HRID 1721597Notes

Reaction equation

HRID 1721597 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:6]2[CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][N:9]([CH3:12])[CH2:10][CH2:11][C:5]=2[C:4]=1[N+:21]([O-:23])=[O:22].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:20]=[CH:19][C:6]2[CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][N:9]([CH3:12])[CH2:10][CH2:11][C:5]=2[C:4]=1[N+:21]([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22413370HCID 22413370, compound

Product 1

HCID 22413361HCID 22413361, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

0.40 g (0.00128 mol) 7-methoxy-3-methyl-6-nitro-l-phenyl-2,3,4,5-tetrahydro1H-3-benzazepine was dissolved in 6 ml dry dichloromethane. The solution was cooled to -20° C. and 1.5 ml boron tribromide was added dropwise. The reaction mixture was stirred at -20° C. for 15 min and at room temperature for 2.5 h. Then, the mixture was concentrated in vacuo and the residue was hydrolized by careful addition of methanol. 10 ml water was added and the solution was heated to reflux for 0.5h. The cooled solution was adjusted to pH 8.5 by addition of NaHCO3 -solution and extracted with dichloromethane. Evaporation of the solvent yielded the compound as a yellow powder.

Workup

  1. concentrationThen, the mixture was concentrated in vacuo
  2. additionthe residue was hydrolized by careful addition of methanol
  3. addition10 ml water was added
  4. temperaturethe solution was heated
  5. temperatureto reflux for 0.5h
  6. additionThe cooled solution was adjusted to pH 8.5 by addition of NaHCO3 -solution
  7. extractionextracted with dichloromethane
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-72a8c8cd1c414de3949a3952ea7c3c14
Source dataset
uspto-grants-1996_04
Patent number
US05512562

Reaction notes

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