Hydrogen Bromide → HCID 57163122, compound

HRID 1166600Notes

Reaction equation

HRID 1166600 reaction equation
[CH:1]1([C:4]2(O)[C:10]3[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:9]=3[O:8][CH2:7][C:6]3[N:17]=[CH:18][CH:19]=[CH:20][C:5]2=3)[CH2:3][CH2:2]1.[BrH:22].O.[OH-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Br:22][CH2:3][CH2:2][CH:1]=[C:4]1[C:10]2[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]2[N:17]=[CH:18][CH:19]=[CH:20][C:5]1=2

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 14798Sodium HydroxideHCID 22998961HCID 22998961, compound

Product 1

HCID 57163122HCID 57163122, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of step 1 (4.3 g) in acetic acid (30 ml) was added 48% aqueous HBr (25 ml) at 10° C. The reaction mixture was warmed to room temperature, and stirred for 12 hours. Water and ethyl acetate were added to the reaction mixture and neutralized with dilute NaOH solution. The organic layer was separated and washed with saturated aqueous sodium chloride, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (1:4) to give 5-(3-bromopropylidene)-5,11-dihydro-7-methoxypyrido[2,3-c][1]benzoxepine (5.6 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with ethyl acetate-hexane (1:4)

Sources & evidence

ORD record
ord-eea6921160d44b488a3a82421b1b86e3
Source dataset
uspto-grants-2003_09
Patent number
US06613905B1

Reaction notes

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