Chlorobenzene → Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoate

HRID 2286678Notes

Reaction equation

HRID 2286678 reaction equation
ClC1C=CC=CC=1.[F:8][C:9]([F:25])([F:24])[C:10]1[CH:23]=[CH:22][C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1.Br[CH:27]([CH:34](Br)[CH3:35])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CC)CCC.O>[F:8][C:9]([F:24])([F:25])[C:10]1[CH:23]=[CH:22][C:13]([O:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH:34]([CH3:35])[CH:27]=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:19][CH:20]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 7964ChlorobenzeneHCID 11430Potassium CarbonateHCID 170230p-(4-(Trifluoromethyl)phenoxy)phenolHCID 12922552Ethyl 3,4-dibromopentanoate

Product 1

HCID 156921Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoateYield 95.2%

Reagents, catalysts & solvents 2

HCID 19043781N,N-Dibutyl-N-ethylbutan-1-aminium bromideCatalystHCID 962WaterSolvent

Procedure

In a reactor, 15 g of chlorobenzene and 15 g of water were charged, and 12.7 g (0.05 mole) of 4-(4-trifluoromethylphenoxy)phenol, 15.8 g (0.055 mole) of ethyl 3,4-dibromopentanoate and 8.7 g (0.063 mole) of potassium carbonate and 0.3 g (0.001 mole) of tributylethylammonium bromide were added. They were refluxed for 6 hours to react them. The water phase was separated and the organic phase was washed with 5% hydrochloric acid and with water and then, chlorobenzene, ethyl 3,4-dibromopentanoate and low boiling by-products were distilled off at 100° C. under a reduced pressure (0.02-0.05 mmHg) to obtain 18.1 g of ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoate (nD20 1.5175). The yield was 95.1%.

Workup

  1. temperatureThey were refluxed for 6 hours
  2. customto react them
  3. customThe water phase was separated
  4. washthe organic phase was washed with 5% hydrochloric acid and with water
  5. distillationchlorobenzene, ethyl 3,4-dibromopentanoate and low boiling by-products were distilled off at 100° C. under a reduced pressure (0.02-0.05 mmHg)

Sources & evidence

ORD record
ord-66aa32489e3a4ccfb619f2bf43f8dfb5
Source dataset
uspto-grants-1981_05
Patent number
US04267317

Reaction notes

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