Methanol → HCID 14719570, compound

HRID 1461850Notes

Reaction equation

HRID 1461850 reaction equation
[F:1][C:2]1[C:7]([CH:8]2[C:17]3[C:12](=[C:13]([O:20]C)[C:14]([O:18]C)=[CH:15][CH:16]=3)[CH2:11][NH:10][CH2:9]2)=[CH:6][C:5]([O:22]C)=[C:4]([O:24]C)[CH:3]=1.B(Br)(Br)[Br:27].ClCCl.CO>ClCCl>[BrH:27].[F:1][C:2]1[C:7]([CH:8]2[C:17]3[C:12](=[C:13]([OH:20])[C:14]([OH:18])=[CH:15][CH:16]=3)[CH2:11][NH:10][CH2:9]2)=[CH:6][C:5]([OH:22])=[C:4]([OH:24])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 199597004-(6-Fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinolineHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 14719570HCID 14719570, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.90 g of 4-(6-fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline was dissolved in 25 ml of dichloromethane; and to the mixture was added dropwise 1M boron tribromide-dichloromethane solution (27 ml) under an argon gas stream, at internal temperature of -30° to -60° C. under cooling while stirring. The mixture was stirred for 3 hours at room temperature, and 7.0 ml of methanol was added to the mixture under cooling with dry ice-methanol bath, dropwise. The mixture was stirred for 30 minutes at room temperature, the crystals which separated out was collected, giving 0.75 g of 4-(6-fluoro-3,4-dihydroxyphenyl)-7,8-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide.

Workup

  1. temperatureat internal temperature of -30° to -60° C. under cooling
  2. stirringThe mixture was stirred for 3 hours at room temperature
  3. temperatureunder cooling with dry ice-methanol bath
  4. stirringThe mixture was stirred for 30 minutes at room temperature
  5. customthe crystals which separated out
  6. customwas collected

Sources & evidence

ORD record
ord-8e031dca3b43440b9f88dea441ccb971
Source dataset
uspto-grants-1991_12
Patent number
US05077406

Reaction notes

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