Bromine → 7-Bromo-2,3,4,5-tetrahydro-8-methoxy-1-phenyl-1H-3-benzazepine

HRID 247437Notes

Reaction equation

HRID 247437 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]=2[CH:20]=1.[Br:21]Br>C(O)(=O)C>[Br:21][C:5]1[C:4]([O:3][CH3:2])=[CH:20][C:8]2[CH:9]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:10][NH:11][CH2:12][CH2:13][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 20160691HCID 20160691, compound

Product 1

HCID 105205537-Bromo-2,3,4,5-tetrahydro-8-methoxy-1-phenyl-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8-Methoxy-1-phenyl-2,3,4,5-tetrahydro-1H3-benzazepine hydrochloride (66 g, 0.23 m) was suspended in acetic acid (300 ml) and treated with bromine (43 g, 0.27 m). The mixture was heated to 95° for one hour, cooled and filtered. The filter cake was partitioned between ethyl acetate and ammonium hydroxide to afford 7-bromo-8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine.

Workup

  1. temperatureThe mixture was heated to 95° for one hour
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filter cake was partitioned between ethyl acetate and ammonium hydroxide

Sources & evidence

ORD record
ord-886e54afc3da44b1956809a5f9513b61
Source dataset
uspto-grants-1987_11
Patent number
US04707483

Reaction notes

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