Bromine → 3-acetyl-8-bromo-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 621446Notes

Reaction equation

HRID 621446 reaction equation
[C:1]([N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:7]=2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Br:17]Br>C(O)(=O)C>[C:1]([N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[C:12]([Br:17])[C:13]([O:15][CH3:16])=[CH:14][C:7]=2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 138533493-acetyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 212428893-acetyl-8-bromo-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 3-acetyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (2.3 g, 0.01 m) in acetic acid (20 ml) was treated with a solution of bromine (1.8 g, 0.011 m) in acetic acid (10 ml). The mixture was warmed to 70° for 1.5 hours, concentrated in vacuo and partitioned between water and ethyl acetate. The ethyl acetate phase was washed, dried with sodium sulfate and concentrated in vacuo to give 3-acetyl-8-bromo-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine. NMR (CDCl3) 6.7, 7.3; aryl protons.

Workup

  1. temperatureThe mixture was warmed to 70° for 1.5 hours
  2. concentrationconcentrated in vacuo
  3. custompartitioned between water and ethyl acetate
  4. washThe ethyl acetate phase was washed
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9098c3c407434601861c0c650b91d1c4
Source dataset
uspto-grants-1989_04
Patent number
US04824839

Reaction notes

Loading…