Hydrochloric Acid → HCID 71077124, compound

HRID 2273372Notes

Reaction equation

HRID 2273372 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:20])[C:5]([C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)([F:11])[F:10])=[C:6]([F:8])[CH:7]=1.[CH2:21]([OH:27])[CH2:22][CH2:23][CH2:24][C:25]#[CH:26].[OH2:28].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:10][C:9]([F:11])([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:3]#[C:2][CH2:7][CH2:6][CH2:5][CH2:4][OH:28])=[CH:15][CH:14]=1)[C:5]1[C:4]([F:20])=[CH:3][C:2]([C:26]#[C:25][CH2:24][CH2:23][CH2:22][CH2:21][OH:27])=[CH:7][C:6]=1[F:8]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 702345-Hexyn-1-olHCID 86677430HCID 86677430, 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

10.7 g (25.8 mmol) of 5-bromo-2-[(4-bromophenoxy)difluoromethyl]-1,3-difluorobenzene and 8.00 g (81.5 mmol) of hex-5-yn-1-ol are initially introduced in 11.3 ml of triethylamine and 500 ml of toluene, 1.50 g (2 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.700 g (3.68 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-a8f1393a185f4616b57203734e315b1a
Source dataset
uspto-grants-2015_09
Patent number
US09120969B2

Reaction notes

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