Boron tribromide → HCID 12773913, compound

HRID 1164544Notes

Reaction equation

HRID 1164544 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 temperature 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-16ed1719b25d43018476d88b75b41083
Source dataset
uspto-grants-1983_01
Patent number
US04370332

Reaction notes

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