Boron tribromide → HCID 20511257, compound

HRID 1658337Notes

Reaction equation

HRID 1658337 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 19 hours at -51° to -20°C. After the reaction, methylene chloride was distilled off under reduced pressure. To the residue were 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 powdery 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 19 hours at -51° to -20°C
  3. distillationwas distilled off under reduced pressure
  4. additionTo the residue were 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 powdery 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-8ccfbdc65f5e4955ab8c6c7ae155450d
Source dataset
uspto-grants-1976_06
Patent number
US03963725

Reaction notes

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