Boron tribromide → HCID 12773913, compound

HRID 1284070Notes

Reaction equation

HRID 1284070 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20]C)=[C:15]([O:18]C)[CH:16]=3)[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.B(Br)(Br)[Br:25]>C(Cl)Cl>[BrH:25].[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:22][CH:23]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10065439HCID 10065439, compound

Product 1

HCID 12773913HCID 12773913, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-chlorophenoxy)methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (90 mg) in anhydrous methylene chloride (5 ml) was added boron tribromide (203 mg) at -55°C under cooling and stirring, and then the reaction temperture was gradually elevated to at 5°C over 17.5 hours. After the reaction, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol (5 ml) and water (0.5 ml), and the solution was warmed at 60° to 80°C for 10 minutes and then the solution was concentrated. 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 (77 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 under reduced pressure
  4. dissolutionThe residue was dissolved in methanol (5 ml)
  5. temperaturewater (0.5 ml), and the solution was warmed at 60° to 80°C for 10 minutes
  6. concentrationthe solution was concentrated
  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-86f598c3cc8c41f0b1c2d00d3c3d899f
Source dataset
uspto-grants-1976_08
Patent number
US03978063

Reaction notes

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