1,2-Dimethoxyethane → HCID 11954577, compound

HRID 2096095Notes

Reaction equation

HRID 2096095 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+].COCCOC>C(OCC)(=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 79599(4-Bromophenyl)boronic acidHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 11954577HCID 11954577, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a 500 mL round bottom flask, 4-bromophenylboronic acid (25.0 g, 0.125), 2-bromo-5-methylpyridine (20.0 g, 0.114 mol), palladium(0)tetrakistriphenylphosphine (4.0 g, 0.0035 mol), potassium carbonate (47.0 g, 0.34 mol.), 1,2 dimethoxyethane (120 mL) and water (120 mL.) were added. The mixture was heated to reflux under nitrogen atmosphere for 18 hours. After the reaction was cooled down, 100 mL of water and 150 mL of ethyl acetate were added. The mixture was separated in a separatory funnel. The organic phases were collected, combined and evaporated. The mixture was distilled using a kugelrohred (spelling?) to obtain 2-(4-bromophenyl)-5-methylpyridine (26.0 g) as a white solid that was further purified by recrystallization in hexanes.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen atmosphere for 18 hours
  3. temperatureAfter the reaction was cooled down
  4. customThe mixture was separated in a separatory funnel
  5. customThe organic phases were collected
  6. customevaporated
  7. distillationThe mixture was distilled

Sources & evidence

ORD record
ord-437fdacbe75241f3865cca802a867d96
Source dataset
uspto-grants-2013_05
Patent number
US08449990B2

Reaction notes

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