Boron tribromide → HCID 12773913, compound

HRID 1284069Notes

Reaction equation

HRID 1284069 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][CH:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:20])=[C:15]([O:18]C)[CH:16]=3)[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.B(Br)(Br)[Br:24]>C(Cl)Cl>[BrH:24].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:20])=[C:15]([OH:18])[CH:16]=3)[CH2:11][CH2:10][NH:9]2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 12821122HCID 12821122, compound

Product 1

HCID 12773913HCID 12773913, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-chlorophenoxy)methyl-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline (100 mg) in anhydrous methylene chloride (5 ml) was added boron tribromide (140 mg) at -60°C under cooling and stirring, and then the reaction temperture was gradually elevated to at 15°C over 22 hours. After the reaction, the reaction mixture was concentrated, and oily residue was dissolved in methanol (5 ml) and water (0.5 ml). The solution was refluxed for 10 minutes, and then the solvent was distilled off. The amorphous residue was dissolved in acetone, and to the solution was added ether, and the mixture was allowed to stand. The precipitated crystals were collected by filtration and dried to give 1-(4-chlorophenoxy)methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (81 mg), mp 232° to 233°C. The product was identified with a sample by I.R. spectrum and N.M.R. spectrum.

Workup

  1. temperatureunder cooling
  2. customAfter the reaction
  3. concentrationthe reaction mixture was concentrated
  4. dissolutionoily residue was dissolved in methanol (5 ml)
  5. temperatureThe solution was refluxed for 10 minutes
  6. distillationthe solvent was distilled off
  7. dissolutionThe amorphous residue was dissolved in acetone
  8. additionto the solution was added ether
  9. filtrationThe precipitated crystals were collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-21782b5ea87c4bf88f2231291e5452a2
Source dataset
uspto-grants-1976_08
Patent number
US03978063

Reaction notes

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