Hydrogen Bromide → 2-Bromo-10,11-dihydro-dibenz[b,f]oxepin-10-one

HRID 866608Notes

Reaction equation

HRID 866608 reaction equation
N[C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1.N([O-])=O.[Na+].C(OCC)(=O)C.[BrH:28]>CS(O)(=O)=O.[Cu]Br>[Br:28][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 227679272-Amino-10,11-dihydro-dibenz[b,f]oxepin-10-oneHCID 23668193Sodium Nitrite

Product 1

HCID 227678432-Bromo-10,11-dihydro-dibenz[b,f]oxepin-10-one

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 6395Methanesulfonic AcidSolvent

Procedure

In an analogous manner to that described in Example 6, 30 g. of 2-amino-10,11-dihydro-dibenz[b,f]oxepin-10-one are diazotized with 12 g. of sodium nitrite in methanesulfonic acid solution. The solution obtained is poured into a mixture of 540 ml. of ethyl acetate and a solution of 57.2 g. of copper (I) bromide in 666 ml. of 48% hydrobromic acid. After 10 minutes, the mixture is worked-up in the same manner as described in Example 6, and there is obtained 2-bromo-10,11-dihydro-dibenz[b,f]oxepin-10-one having a melting point of 53°-54° C. The product is reacted further in an analogous manner to that described in Example 1 to give the desired starting material, 1-[2-bromo-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-piperazine having a melting point of 93°-94° C. The following intermediates are obtained:

Workup

  1. customThe solution obtained
  2. additionis poured into a mixture of 540 ml

Sources & evidence

ORD record
ord-7f454d1386384f958f03917b5518cdca
Source dataset
uspto-grants-1978_07
Patent number
US04100173

Reaction notes

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