Bromine → HCID 9968598, compound

HRID 1057361Notes

Reaction equation

HRID 1057361 reaction equation
[Br:1][C:2]1[C:3]([O:23][CH3:24])=[CH:4][C:5]2[N:11]([CH2:12][CH3:13])[C:10](=[O:14])[CH:9]([C:15]([O:17][C:18](C)(C)C)=[O:16])[CH2:8][CH2:7][C:6]=2[CH:22]=1.BrBr>CO>[Br:1][C:2]1[C:3]([O:23][CH3:24])=[CH:4][C:5]2[N:11]([CH2:12][CH3:13])[C:10](=[O:14])[CH:9]([C:15]([O:17][CH3:18])=[O:16])[CH2:8][CH2:7][C:6]=2[CH:22]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 10111450HCID 10111450, compound

Product 1

HCID 9968598HCID 9968598, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

When 7-bromo-3(R,S)-tert-butoxycarbonyl-1-ethyl-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one was treated with bromine in MeOH at ambient temperature, bromination occurred at 3-position of the 1-benzazepine-2-one ring system. In addition, a transesterification due to the presence of methanol was observed which resulted in a formation of 7-bromo-3(R,S)-methoxycarbonyl-1-ethyl-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one.

Sources & evidence

ORD record
ord-597607844d314bab9077d223a5c6b6b8
Source dataset
uspto-grants-2003_02
Patent number
US06514965B1

Reaction notes

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