Boron tribromide → HCID 20511257, compound

HRID 1164546Notes

Reaction equation

HRID 1164546 reaction equation
C[O:2][C:3]1[CH:24]=[CH:23][C:6]([O:7][CH2:8][CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21]C)=[C:16]([O:19]C)[CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.B(Br)(Br)[Br:26]>C(Cl)Cl>[BrH:26].[OH:2][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:21])=[C:16]([OH:19])[CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 4120006HCID 4120006, compound

Product 1

HCID 20511257HCID 20511257, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1-(4-methoxyphenoxy)methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (100 mg) in anhydrous methylene chloride (5 ml) was added a solution of boron tribromide (300 mg) in anhydrous methylene chloride (0.6 ml) at -51° C. under cooling and stirring, and the mixture was stirred for 10 hours at -51° to -20° C. After the reaction, methylene chloride was distilled off under reduced pressure. To the residue was added methanol (5 ml) and water (0.5 ml) and the mixture was warmed, and then the solvent was distilled off under reduced pressure. The colourless powderly residue was dissolved in acetone, and then to the solution was added ether, and the mixture was allowed to stand. The precipitated crystals were collected by filtration to give colourless powder of 1-(4-hydroxyphenoxy)methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide.

Workup

  1. temperatureunder cooling
  2. stirringthe mixture was stirred for 10 hours at -51° to -20° C
  3. distillationwas distilled off under reduced pressure
  4. additionTo the residue was added methanol (5 ml) and water (0.5 ml)
  5. temperaturethe mixture was warmed
  6. distillationthe solvent was distilled off under reduced pressure
  7. dissolutionThe colourless powderly residue was dissolved in acetone
  8. additionto the solution was added ether
  9. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-b529f5f70160486e8fb8d7c474248aef
Source dataset
uspto-grants-1983_01
Patent number
US04370332

Reaction notes

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