Boron tribromide → HCID 20316636, compound

HRID 2419022Notes

Reaction equation

FC(F)(F)C1C(OC)=C(OC)C=CC=1CCN.FC(F)(F)C1C(OC)=C(OC)C=CC=1C.[F:33][C:34]([F:59])([F:58])[C:35]1[C:45]2[CH2:44][CH2:43][NH:42][CH2:41][CH:40]([C:46]3[CH:51]=[CH:50][C:49]([S:52][CH3:53])=[CH:48][CH:47]=3)[C:39]=2[CH:38]=[C:37]([O:54]C)[C:36]=1[O:56]C.B(Br)(Br)Br>>[F:59][C:34]([F:33])([F:58])[C:35]1[C:45]2[CH2:44][CH2:43][NH:42][CH2:41][CH:40]([C:46]3[CH:47]=[CH:48][C:49]([S:52][CH3:53])=[CH:50][CH:51]=3)[C:39]=2[CH:38]=[C:37]([OH:54])[C:36]=1[OH:56]

Participants

Reactant 4

HCID 25134Boron tribromide

HCID 20316661HCID 20316661, compound

HCID 20347751HCID 20347751, compound

HCID 20518141HCID 20518141, compound

Product 1

HCID 20316636HCID 20316636, compound

Procedure

Substituting a stoichiometric quantity of 2-fluoro-3,4-dimethoxyphenethylamine in the synthetic procedures of Example 1 gives 6-fluoro-7,8-dimethoxy-1-(p-methylthiophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine. Hydrolysis with boron tribromide as disclosed above gives 6-fluoro-7,8-dihydroxy-1 -(p-methylthiophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine. Substituting 2-trifluoromethyl-3,4,-dimethoxyphenethylamine, prepared via 2-trifluoromethyl-3,4,-dimethoxytoluene, in Example 1 gives 6-trifluoromethyl-7,8-dimethoxy-1-(p-methylthiophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine and hydrolysis with boron tribromide gives 6-trifluoromethyl-7,8-dihydroxy-1-(p-methylthiophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine.

Workup

customgives

Sources & evidence

ORD record: ord-041668a62e5c42848ad500d680270f84
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04104379

Reaction notes

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