HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

1,2-Dimethoxyethane → 2-Chloro-4-(4-methylphenyl)pyridine

HRID 1844937
Notes
Print preview

Reaction equation

HRID 1844937 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[C:9]1([CH3:24])[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1C1C=CC(B(O)O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:12]2[CH:13]=[CH:14][C:9]([CH3:24])=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 15165112-Chloro-4-iodopyridineHCID 23005382(2'-Methyl-[1,1'-biphenyl]-4-yl)boronic acid

Product 1

HCID 446052162-Chloro-4-(4-methylphenyl)pyridineYield 44%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent

Procedure

A mixture of 2-chloro-4-iodopyridine (10.0 g, 41.8 mmol), p-tolylphenylboronic acid (5.68 g, 41.8 mmol), Pd(Ph3P)4 (1.45 g 1.25 mmol), sodium carbonate (13.3 g, 125 mmol), DME (300 mL) and water (75 mL) was degassed with nitrogen and then refluxed overnight. The reaction mixture was concentrated and extracted with ethyl acetate. The ethyl acetate layer was dried on Na2SO4 and vacuum distilled and recrystallized to give 2-chloro-4-(p-tolyl)pyridine (3.75 g, 18.4 mmol, 44% yield).

Workup

  1. customwas degassed with nitrogen
  2. temperaturerefluxed overnight
  3. concentrationThe reaction mixture was concentrated
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried on Na2SO4 and vacuum
  6. distillationdistilled
  7. customrecrystallized

Sources & evidence

ORD record
ord-58f2a078846c46cdb49b5a6dc4f3072b
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946697B1

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes