Boron tribromide → HCID 12833521, compound

HRID 2058998Notes

Reaction equation

[Br:1][C:2]1[C:12]2[CH2:11][CH2:10][NH:9][CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[C:6]=2[CH:5]=[C:4]([O:21]C)[C:3]=1[O:23]C.B(Br)(Br)Br>>[BrH:1].[Br:1][C:2]1[C:12]2[CH2:11][CH2:10][NH:9][CH2:8][CH:7]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)[C:6]=2[CH:5]=[C:4]([OH:21])[C:3]=1[OH:23]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 12624818HCID 12624818, compound

Product 1

HCID 12833521HCID 12833521, compound

Procedure

Substituting a stoichiometric quantity of 2-fluoro-3,4-dimethoxyphenethylamine in the synthetic procedure of Example 1 gave 6-fluoro-7,8-dimethoxy-1-(1-methoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine as a yellow oil. Hydrolysis with boron tribromide gave 6-fluoro-7,8-dihydroxy-1-(p-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide, m.p. 277° (dec.). Substituting appropriate bromo starting material in the methods described herein gave 6-bromo-7,8-dimethoxy-1-(p-methoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine then hydrolysis with boron tribromide gave 6-bromo-7,8-dihydroxy-1(p-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide, m.p. 254° (dec.).

Sources & evidence

ORD record: ord-2b4a85f5774e4a97a2f01a00c1e1ee43
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04321195

Reaction notes

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