Methanol → 4-(6-Fluoro-3,4-dihydroxyphenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrobromide

HRID 1089490Notes

Reaction equation

HRID 1089490 reaction equation
[F:1][C:2]1[C:7]([CH:8]2[CH2:13][NH:12][CH2:11][C:10]3[S:14][CH:15]=[CH:16][C:9]2=3)=[CH:6][C:5]([O:17]C)=[C:4]([O:19]C)[CH:3]=1.B(Br)(Br)[Br:22].ClCCl.CO>ClCCl>[BrH:22].[F:1][C:2]1[C:7]([CH:8]2[CH2:13][NH:12][CH2:11][C:10]3[S:14][CH:15]=[CH:16][C:9]2=3)=[CH:6][C:5]([OH:17])=[C:4]([OH:19])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 199597114-(6-Fluoro-3,4-dimethoxyphenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridineHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 199597144-(6-Fluoro-3,4-dihydroxyphenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrobromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.65 g of 4-(6-fluoro-3,4-dimethoxyphenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine was dissolved in 14 ml of dichloromethane; and to the mixture was added 1M boron tribromide-dichloromethane solution (12 ml) dropwise under an argon gas stream, while cooling at -30°--60° C. (internal temperature) while stirring. The mixture was stirred for 2 hours at room temperature, and 20 ml of methanol was added dropwise thereto under ice cooling. The solvent was distilled off, and the residue obtained was crystallized by using a mixture of methanol and chloroform (1:8). The crystals were collected by filtration, and recrystallized from ethanol, giving 0.29 g of 4-(6-fluoro-3,4-dihydroxyphenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrobromide.

Workup

  1. temperaturewhile cooling at -30°--60° C. (internal temperature)
  2. stirringThe mixture was stirred for 2 hours at room temperature
  3. distillationThe solvent was distilled off
  4. customthe residue obtained
  5. customwas crystallized
  6. additiona mixture of methanol and chloroform (1:8)
  7. filtrationThe crystals were collected by filtration
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4fd8bb41ff364c7eaa17e51b76f92187
Source dataset
uspto-grants-1990_10
Patent number
US04966904

Reaction notes

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