3-Bromophenol → 1-Bromo-3-(2,2,2-trifluoroethoxy)benzene

HRID 2110154Notes

Reaction equation

HRID 2110154 reaction equation
CC1C=CC(S(O[CH2:12][C:13]([F:16])([F:15])[F:14])(=O)=O)=CC=1.[Br:17][C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1.[OH-].[Na+]>CN(C)C=O>[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:12][C:13]([F:16])([F:15])[F:14])[CH:19]=1

Participants

5

Reactant 3

HCID 115633-BromophenolHCID 14798Sodium HydroxideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)

Product 1

HCID 247053311-Bromo-3-(2,2,2-trifluoroethoxy)benzeneYield 74.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (3 g, 11.81 mmol) in dimethylformamide (20 mL) was added 3-bromophenol (1 g, 5.78 mmol) and NaOH (500 mg, 12.50 mmol). The resulting solution was stirred at 100° C. for 3 h. The reaction mixture was quenched by the adding H2O (100 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried (Na2SO4) and concentrated, and the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether) to provide 1.1 g (31%) of 1-bromo-3-(2,2,2-trifluoroethoxy)benzene.

Workup

  1. customThe reaction mixture was quenched by the adding H2O (100 mL)
  2. extractionextracted with methylene chloride (3×50 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-dfd9b773df2841b2829dad0c8afac38d
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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