4-Bromodiphenyl Ether → 4-Phenoxythiophenol

HRID 1584377Notes

Reaction equation

HRID 1584377 reaction equation
C[S-:2].[Na+].[CH:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CN(C)C=O>[O:10]([C:11]1[CH:16]=[CH:15][C:14]([SH:2])=[CH:13][CH:12]=1)[C:7]1[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 75654-Bromodiphenyl EtherHCID 14798Sodium HydroxideHCID 4378561Sodium methanethiolate

Product 1

HCID 27603544-Phenoxythiophenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of sodium thiomethoxide (25 g) and 4-bromodiphenyl ether (25 g) in N,N-dimethylformamide (DMF) (150 ml) was refluxed overnight. The mixture was cooled and added to dilute aqueous sodium hydroxide. The water layer was washed with ether to remove by-products and acidified with hydrochloric acid. The product, 4-(phenoxy)thiophenol, was extracted with ether, and the ether layer dried and evaporated to give 4-(phenoxy)thiophenol (19-20 g) as a red oil. This material can be used without further purification.

Workup

  1. temperatureThe mixture was cooled
  2. washThe water layer was washed with ether
  3. customto remove by-products
  4. extractionThe product, 4-(phenoxy)thiophenol, was extracted with ether
  5. dry with materialthe ether layer dried
  6. customevaporated

Sources & evidence

ORD record
ord-a6aba2dfd74044c49c81ea8fa9aa4cb5
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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