Water → 4-Bromo-2-nitro-1-phenoxybenzene

HRID 16175

Reaction equation

HRID 16175 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[C:7]1([OH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].O>C1COCC1.C(OCC)(=O)C>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([O:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:16]([N+:22]([O-:24])=[O:23])[CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 10796Cesium carbonateHCID 770041,4-Dibromo-2-nitrobenzene

Product 1

HCID 161094494-Bromo-2-nitro-1-phenoxybenzeneYield 108.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cs2CO3 (4 g, 12.3 mmol) was added to a solution of phenol (1 g, 10.6 mmol) in 50 mL of THF under N2 atmosphere. After stirring for 15 min. 1,4-dibromo-2-nitrobenzene (2.81 g, 10 mmol) was added. The resulting mixture was heated to reflux and stirred overnight at reflux. Water and ethyl acetate were added, followed by extraction with ethyl acetate (3×). The combined organic layers were washed with water and brine, dried (Na2SO4) and evaporated to give the crude compound (3.2 g, 75%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. stirringstirred overnight
  4. temperatureat reflux
  5. extractionfollowed by extraction with ethyl acetate (3×)
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-efae84e757614749b3b88bf9a2fe4d09
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Linked notes

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