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Phosphorus tribromide → 1-(2-Bromo-4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene

HRID 324037
Notes
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Reaction equation

HRID 324037 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[C:10]([C:22]([O:24][CH3:25])=[O:23])[C:9]=2[C:26]([O:28][CH3:29])=[O:27])[CH:5]=[CH:4][N:3]=1.P(Br)(Br)[Br:31]>ClC(Cl)C(Cl)Cl>[Br:31][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[C:10]([C:22]([O:24][CH3:25])=[O:23])[C:9]=2[C:26]([O:28][CH3:29])=[O:27])[CH:5]=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 220073311-(2-Chloro-4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene

Product 1

HCID 220073291-(2-Bromo-4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene

Reagents, catalysts & solvents 1

HCID 65911,1,2,2-TetrachloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(2-chloro-4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene (22.7 g), phosphorus tribromide (52 ml) and 1,1,2,2-tetrachloroethane (100 ml) is stirred at 100° C. for 10 hours. After the reaction is complete, the mixture is concentrated under reduced pressure to remove the solvent, and thereto are added methylene chloride and an aqueous potassium carbonate solution. The methylene chloride layer is separated, and concentrated under reduced pressure to remove the solvent. The residue is crystallized from methanol to give 1-(2-bromo-4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene (17.1 g).

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. customto remove the solvent
  3. additionare added methylene chloride
  4. customThe methylene chloride layer is separated
  5. concentrationconcentrated under reduced pressure
  6. customto remove the solvent
  7. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-bb898cb610164bfa94f883316c7c5530
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06214996B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes