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

HRID 542733Notes

Reaction equation

HRID 542733 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) is treated with a solution of bromine (1.8 g, 0.011 m) in acetic acid (10 ml). The mixture is warmed to 70° for 1.5 hours, concentrated in vacuo and partitioned between water and ethyl acetate. The ethyl acetate phase is 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.

Workup

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

Sources & evidence

ORD record
ord-f27f01b034b6452cb205d456fa16d1f2
Source dataset
uspto-grants-1987_04
Patent number
US04659706

Reaction notes

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