Hydrochloric Acid → HCID 67123175, compound

HRID 2168851Notes

Reaction equation

HRID 2168851 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1)#[CH:10].C(OCC)(=O)C.Cl>C1COCC1.C(NC(C)C)(C)C.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.[Cu]I>[OH:16][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([C:9]#[C:10][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[CH:12][CH:13]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 78084-BromophenolHCID 8857Ethyl AcetateHCID 11170993(4-Ethynylphenyl)methanol

Product 1

HCID 67123175HCID 67123175, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 7912DiisopropylamineSolventHCID 8028TetrahydrofuranSolvent

Procedure

6.50 g (37.6 mmol) of 4-bromophenol and 5.00 g (37.8 mmol) of 4-ethynylbenzyl alcohol are initially introduced in 70 ml of THF and 10 ml of diisopropylamine, and, after addition of 1.50 g (2.14 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.40 g (2.10 mmol) of copper(I) iodide, the mixture is heated under reflux overnight. After addition of 100 ml of ethyl acetate, the mixture is acidified using 2 M hydrochloric acid, the aqueous phase is extracted three times with ethyl acetate, and the combined org. phases are dried over sodium sulfate. The solvent is removed in vacuo, and the residue is purified by chromatography on silica gel, giving 4-(4-hydroxymethylphenylethynyl)phenol as a colourless solid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. extractionthe aqueous phase is extracted three times with ethyl acetate
  4. dry with materialphases are dried over sodium sulfate
  5. customThe solvent is removed in vacuo
  6. customthe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c8254bb7423d4583aee54cc671773891
Source dataset
uspto-grants-2015_06
Patent number
US09045683B2

Reaction notes

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