2,4,6-Tribromophenol → HCID 18448747, compound

HRID 1269574

Reaction equation

HRID 1269574 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([Br:9])[C:3]=1[OH:10].F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:8][C:6]1[CH:7]=[C:2]([Br:1])[C:3]([O:10][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[C:4]([Br:9])[CH:5]=1

Participants

5

Reactant 3

HCID 14832,4,6-TribromophenolHCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonate

Product 1

HCID 18448747HCID 18448747, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 2,4,6-tribromophenol (3.8 g), 4-fluoronitrobenzene (1:6 g), cesium carbonate (3.7 g) in dimethylformamide (8 mL) was heated at reflux until the starting materials were consumed. The reaction was cooled to room temperature and concentrated. The residue was dissolved in ethyl acetate and washed with sodium hydroxide (2 N), hydrochloric acid (2 N) and brine. Concentration of the organic phase gave 1,3,5-tribromo-4-(4-nitrophenoxy)benzene in quantitative yield. The crude product was used directly in the next step.

Workup

  1. temperatureat reflux until the starting materials
  2. customwere consumed
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with sodium hydroxide (2 N), hydrochloric acid (2 N) and brine

Sources & evidence

ORD record
ord-f7d8a15e89044a28844d345b9cd75f4f
Source dataset
uspto-grants-2007_04
Patent number
US07199265B2

Linked notes

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