Hydrochloric Acid → HCID 71077124, compound

HRID 630564Notes

Reaction equation

HRID 630564 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([F:14])[C:11]([C:15]([F:25])([F:24])[O:16][C:17]3[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=3)=[C:10]([F:26])[CH:9]=2)=[C:4](F)[CH:3]=1.[CH2:28]([OH:34])[CH2:29][CH2:30][CH2:31][C:32]#[CH:33].[OH2:35].Cl>C(N(CC)CC)C.C1(C)C=CC=CC=1.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>[F:25][C:15]([F:24])([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:33]#[C:32][CH2:31][CH2:30][CH2:29][CH2:28][OH:34])=[CH:19][CH:18]=1)[C:11]1[C:12]([F:14])=[CH:13][C:8]([C:5]#[C:4][CH2:3][CH2:2][CH2:7][CH2:6][OH:35])=[CH:9][C:10]=1[F:26]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 702345-Hexyn-1-olHCID 86717690HCID 86717690, compound

Product 1

HCID 71077124HCID 71077124, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

6.00 g (10.8 mmol) of 4′-bromo-4-[difluoro-(4-iodophenoxy)methyl]-3,5,2′-trifluorobiphenyl and 4.00 g (40.8 mmol) of hex-5-yn-1-ol are initially introduced in 6 ml of triethylamine and 300 ml of toluene, 0.700 g (1.00 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.100 g (0.525 mmol) of copper(I) iodide are added, and the mixture is heated under reflux overnight. The batch is subsequently added to water, neutralised using 2 N hydrochloric acid and extracted three times with toluene. The combined org. phases are dried over sodium sulfate, the solvent is removed in vacuo, and the residue is chromatographed on silica gel firstly with toluene and then with toluene/ethyl acetate (4:1), giving 6-(4-{difluoro-[4-(6-hydroxyhex-1-ynyl)phenoxy]methyl}-3,5-difluorophenyl)hex-5-yn-1-ol as a colourless solid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. extractionextracted three times with toluene
  4. dry with materialphases are dried over sodium sulfate
  5. customthe solvent is removed in vacuo
  6. customthe residue is chromatographed on silica gel firstly with toluene

Sources & evidence

ORD record
ord-bbce33c96da54d98abac7396ff659f18
Source dataset
uspto-grants-2016_04
Patent number
US09315729B2

Reaction notes

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