Boron tribromide → HCID 22905051, compound

HRID 865337Notes

Reaction equation

HRID 865337 reaction equation
[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:11]=[CH:12][C:13]([O:15]C)=[CH:14][C:6]=2[C:5]1=[O:17])[CH:2]=[CH2:3].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:6]=2[C:5]1=[O:17])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 229049982-allyl-8-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one

Product 1

HCID 22905051HCID 22905051, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-allyl-8-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one (1.10 g, 0.0047 mol) in CH2Cl2 (20 mL) was treated at 0° C. with BBr3 (1M in CH2Cl2, 9.50 mL), and the resulting mixture stirred at (0° C. for 30 minutes. The solution was poured over ice, NaHCO3 was added, and the solution was extracted with CH2Cl2. The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo to yield ca. 1.0 g (100%) of 2-allyl-8-hydroxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one as a colorless oil; 1H NMR(CDCl3) d8.2(brs, 1H), 7.47(s, 1H), 6.95(d, J=6 Hz, 1H), 6.84(dd, J=3, 6 Hz, 1H), 5.89(m, 1H), 5.22(m, complex, 2H), 4.20(d, J=6 Hz, 2H), 3.18(t, J=6 Hz, 2H), 2.66(t, J=6 Hz, 2H), 2.15(s, 1H), 1.96(m, 2H); 13C NMR(CDCl3) d171.65(CO), 156.01, 135.6,8, 133.27, 129.55, 128.46, 118.51, 118.05, 115.91, 53.46, 49.81, 45.83, 30.87, 29.76, 29.12.

Workup

  1. additionwas added
  2. extractionthe solution was extracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f75cbbe24c484c3fa4742487581f73a6
Source dataset
uspto-grants-1996_10
Patent number
US05565449

Reaction notes

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