4-Bromo-2-(trifluoromethoxy)iodobenzene → HCID 18751419, compound

HRID 1838017Notes

Reaction equation

HRID 1838017 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([O:9][C:10]([F:13])([F:12])[F:11])[CH:3]=1.CC(O)(C)[C:16]#[C:17][C:18]1[CH:27]=[CH:26][C:21]([O:22][CH2:23][CH2:24][OH:25])=[CH:20][CH:19]=1>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:16]#[C:17][C:18]2[CH:27]=[CH:26][C:21]([O:22][CH2:23][CH2:24][OH:25])=[CH:20][CH:19]=2)=[C:4]([O:9][C:10]([F:13])([F:12])[F:11])[CH:3]=1

Participants

7

Reactant 2

HCID 27364224-Bromo-2-(trifluoromethoxy)iodobenzeneHCID 18751418HCID 18751418, compound

Product 1

HCID 18751419HCID 18751419, compoundYield 82%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A flask equipped with a stirrer and a thermometer was charged with 3.35 g (9.13 mmol) of 4-bromo-2-(trifluoromethoxy)iodobenzene and 19 ml of triethylamine under a nitrogen atmosphere. Then 1.48 g (9.13 mmol) of 2-[4-(3-methyl-3-hydroxybutyne-1-yl)phenoxy]ethanol, 13.7 mg (0.072 mmol) of copper (I) iodide, 63.2 mg (0.24 mmol) of triphenylphosphine, and 13.7 mg (0.020 mmol) of dichlorobis(triphenylphosphine)palladium were added at room temperature, and stirred under reflux for 6 hours. After the insolubles were filtered off and the solvent was distilled off, ethyl acetate was added to the resulting distillate, and the pH was adjusted to an acidity with 1N hydrochloric acid to effect ethyl acetate extraction. The resulting extract was washed with NaCl saturated water, dried over anhydrous sodium sulfate, filtered, and concentrated to thereby obtain 3.85 g of a crude product in the form of a yellowish brown solid. The crude product was then purified by silica gel column chromatography using hexane/ethyl acetate as an eluting solvent to obtain 3.0 g of 2-(4-{2-[4-bromo-2-(trifluoromethoxy)phenyl]ethynyl}phenoxy)ethanol in the form of a light yellow solid in a 82% yield.

Workup

  1. customA flask equipped with a stirrer
  2. temperatureunder reflux for 6 hours
  3. filtrationAfter the insolubles were filtered off
  4. distillationthe solvent was distilled off
  5. additionethyl acetate was added to the resulting distillate, and the pH
  6. extractionethyl acetate extraction
  7. extractionThe resulting extract
  8. washwas washed with NaCl saturated water
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto thereby obtain 3.85 g of a crude product in the form of a yellowish brown solid
  13. customThe crude product was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-90e01663831d40568edc0c1eca4743a4
Source dataset
uspto-grants-2004_01
Patent number
US06673267B2

Reaction notes

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