Toluene → 1-(4-Bromophenoxy)-3-(trifluoromethyl)benzene

HRID 973893Notes

Reaction equation

HRID 973893 reaction equation
[OH-].[K+].[F:3][C:4]([F:13])([F:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1.C1(C)C=CC=CC=1.[Br:21][C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=1>O>[F:3][C:4]([F:12])([F:13])[C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[O:11][C:25]1[CH:26]=[CH:27][C:22]([Br:21])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 73763-(Trifluoromethyl)phenolHCID 78041,4-DibromobenzeneHCID 14797Potassium Hydroxide

Product 1

HCID 136674611-(4-Bromophenoxy)-3-(trifluoromethyl)benzeneYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The reaction is performed in a 1 L 3-necked flask equipped with a mechanical stirrer, a Dean-Stark trap topped with a condenser and a nitrogen bubbler, and a stopper. The flask is flushed with nitrogen and charged firstly with potassium hydroxide (22.4 g, 0.4 mol), α,α,α-trifluoro-m-cresol (64.8 g, 0.4 mol), and toluene (500 mL). The mixture is stirred and heated at reflux for 2 h, during which water collected in the trap (ca. 6 mL). 1,4-Dibromobenzene (94.4 g, 0.42 mol) and cuprous chloride (39.6 g, 0.4 mol) are added, and heating a reflux is continued for another 18 h. The reaction mixture is analyzed by capillary GC which shows ca.45% of the title product along with ca.10% of the dialkylation product, with the rest being starting materials. The mixture is filtered with the aid of ether (200 mL), and washed successively with 2×100 mL portions of 5% HCl (to remove any residual copper impurities), water, and brine. It is then dried (MgSO4) and concentrated on the rotary evaporator to a red oily residue. TLC (silica gel) shows four components (Rf =0.00, 0.15, 0.35, 0.70, CH2Cl2). Fractional distillation afforded 42.9 g (34%) of the title compound, distilling at 112-116° C. @ 1 mm. Also obtained was 12.1 g (10.5%) of the dialkylation product, distilling at 160-165° C. @ 1 mm.

Workup

  1. customThe reaction is performed in a 1 L 3-necked flask
  2. customequipped with a mechanical stirrer
  3. customa Dean-Stark trap topped with a condenser
  4. customThe flask is flushed with nitrogen
  5. temperatureheated
  6. customcollected in the trap (ca. 6 mL)
  7. temperatureheating a reflux

Sources & evidence

ORD record
ord-66b7ddecfe6144b3b184e4225aa17ec9
Source dataset
uspto-grants-1991_11
Patent number
US05066409

Reaction notes

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