Water → HCID 58745549, compound

HRID 1844726Notes

Reaction equation

HRID 1844726 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4](Br)[CH:3]=1.[CH3:13][O-:14].[Na+].O>CN(C=O)C.[Cu]I>[Br:1][C:2]1[CH:3]=[C:4]([O:14][CH3:13])[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 27611701,3-dibromo-5-tert-butylbenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 58745549HCID 58745549, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1,3-dibromo-5-tert-butylbenzene (289 mg, 1 mmol) in DMF (20 mL) were added NaOMe (2 eq) and CuI (0.03 eq). The mixture was stirred at 80° C. for 3 h and then was poured into water and extracted with EA. The combined organic layers were washed with brine and dried over Na2SO4. After filtration, the filtrate was evaporated to give compound 14a as solid (200 mg, 82%).

Workup

  1. extractionextracted with EA
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-58ad272b773d4da4bb8db892f13e510c
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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