1,2-Dibromobenzene → 1-(4-Bromophenoxy)-3,5-di-tert-butylbenzene

HRID 461878

Reaction equation

HRID 461878 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([OH:17])[CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)([CH3:6])([CH3:5])[CH3:4].[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1Br>[Cu].CC(N(C)C)=O>[C:13]([C:11]1[CH:10]=[C:9]([CH:8]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[CH:12]=1)[O:17][C:22]1[CH:23]=[CH:24][C:19]([Br:18])=[CH:20][CH:21]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 114141,2-DibromobenzeneHCID 24758Sodium hydrideHCID 708253,5-Di-tert-butylphenol

Product 1

HCID 203213631-(4-Bromophenoxy)-3,5-di-tert-butylbenzene

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 31374DimethylacetamideSolvent

Procedure

To a suspension of 8.8 g. of 50% sodium hydride (mineral oil dispersion) in 320 ml. of dry dimethylacetamide is added, in portions over 15 minutes with vigorous stirring, 32 g. of 3,5-di-tertiary butylphenol, during which the reaction mixture is cooled with an icebath to moderate the internal temperature. The reaction mixture is then stirred at room temperature for 1 hour, after which is added 75.2 g. of dibromobenzene and 800 mg. of copper powder. The resultant mixture is refluxed for 8 hours, after which time it is cooled and the dimethylacetamide is removed in vacuo. The resultant residue is extracted several times with methylene chloride and the insoluble copper filtered off. The combined methylene chloride extracts are washed two times with water, dried over sodium sulfate, filtered, evaporated in vacuo to dryness and the residue recrystallized from ethanol to obtain 1-(3,5-di-tertiary butylphenoxy)-4-bromobenzene, m.p. 98°-100° C.

Workup

  1. additionTo a suspension of 8.8 g
  2. additionafter which is added 75.2 g
  3. temperatureafter which time it is cooled
  4. customthe dimethylacetamide is removed in vacuo
  5. extractionThe resultant residue is extracted several times with methylene chloride
  6. filtrationthe insoluble copper filtered off
  7. washThe combined methylene chloride extracts are washed two times with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo to dryness
  11. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-bdff0af48ec0419193c4bbbeea246f7d
Source dataset
uspto-grants-1977_12
Patent number
US04064273

Linked notes

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