Boron tribromide → p-{5-[(2-Chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-2-nitrophenoxy}phenol

HRID 21511Notes

Reaction equation

HRID 21511 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([O:18][C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)[CH:10]=2)[CH:5]=[C:4]([F:27])[C:3]=1[C:28]([F:31])([F:30])[F:29].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([CH:10]=2)[O:18][C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)[CH:5]=[C:4]([F:27])[C:3]=1[C:28]([F:31])([F:29])[F:30]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 867487124-[(2-Chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-2-(p-methoxyphenoxy)-1-nitrobenzene

Product 1

HCID 86748713p-{5-[(2-Chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-2-nitrophenoxy}phenolYield 62.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 4-[(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy]-2-(p-methoxyphenoxy)-1-nitrobenzene (12.4 g, 0.027 mol) in methylene chloride is cooled to -78° C., treated with boron tribromide (68 mL of a 1M solution in methylene chloride, 0.068 mol), stirred at -78° C. for two hours, warmed to room temperature and poured onto cracked ice. After the ice has melted, the phases are separated and the aqueous phase is extracted with methylene chloride. The organic phase is combined with the organic extracts and the resultant organic solution is washed with brine and dried over anhydrous sodium sulfate. Silica gel (5 g) is added to the dried organic solution and the mixture is concentrated in vacuo to obtain a brown powder. The powder is placed on top of silica gel in a flash chromatography column and eluted with a (1:1) ether/hexanes solution to give the title product as a brown oil (7.5 g) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. temperaturewarmed to room temperature
  2. additionpoured
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted with methylene chloride
  5. washthe resultant organic solution is washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. additionSilica gel (5 g) is added to the dried organic solution
  8. concentrationthe mixture is concentrated in vacuo
  9. customto obtain a brown powder
  10. washeluted with a (1:1) ether/hexanes solution

Sources & evidence

ORD record
ord-9f60d5c7a383418895395ffe7d11e22f
Source dataset
uspto-grants-1995_06
Patent number
US05424280

Reaction notes

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