Toluene → HCID 10686936, compound

HRID 973895Notes

Reaction equation

HRID 973895 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][CH:25]=[C:24](Br)[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:24]1[CH:23]=[C:22]([Br:21])[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 73763-(Trifluoromethyl)phenolHCID 79271,3-DibromobenzeneHCID 14797Potassium Hydroxide

Product 1

HCID 10686936HCID 10686936, compoundYield 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 time water collected in the trap (ca. 6mL). 1,3-Dibromobenzene (50 mL, 0.42 mol) and cuprous chloride (39.6 g, 0.4 mol) are added to the reaction mixture, and heating at reflux is continued for another 18 h. Then it is analyzed by capillary GC, which shows ca.45% of the title product along with ca.12.5% of the product resulting from dialkylation, with the rest being starting materials. The reaction 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 dried with (MgSO4) and concentrated on the rotary evaporator to a red oily residue. Fractional distillation afforded 47 g (38%) of the title compound, distilling at 113-117° C. @ 1 mm. Also, 112 g (10.5%) of the dialkylation product is obtained, distilling at 160-165° C. @ 1 mm. Other fractions from the distillation show mixtures containing the desired product, but no further effort is made to obtain the rest of it.

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. 6mL)
  7. temperatureheating
  8. temperatureat reflux

Sources & evidence

ORD record
ord-260113ac66db46db88d027dee45d1abc
Source dataset
uspto-grants-1991_11
Patent number
US05066409

Reaction notes

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