Hydrochloric Acid → HCID 68109197, compound

HRID 1429280Notes

Reaction equation

HRID 1429280 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:15]([OH:19])[CH2:16][C:17]#[CH:18].C(NC(C)C)(C)C.Cl>C1COCC1.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.O.CCOCC>[OH:19][CH2:15][CH2:16][C:17]#[C:18][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 135663-Butyn-1-OLHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 68109197HCID 68109197, compound

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

17.2 g (69.0 mmol) of 4-bromo-4′-hydroxybiphenyl, 10.0 g (143 mmol) of but-3-yn-1-ol, 2.00 g (2.85 mmol) of bis(triphenylphosphine)palladium(II) chloride, 0.7 g of copper(I) iodide and 25 ml (178 mmol) of diisopropylamine are heated under reflux overnight in 150 ml of THF. The batch is subsequently added to 200 ml of MTB ether, 400 ml of water are added, and the mixture is acidified using hydrochloric acid. The aqueous phase is separated off and extracted three times with ethyl acetate. The combined org. phases are evaporated in vacuo, and the residue is filtered through silica gel with dichloromethane/ethyl acetate (3:1). Crystallisation of the crude product from toluene gives 4′-(4-hydroxybut-1-ynyl)biphenyl-4-ol as a colourless solid.

Workup

  1. additionare added
  2. customThe aqueous phase is separated off
  3. extractionextracted three times with ethyl acetate
  4. customphases are evaporated in vacuo
  5. filtrationthe residue is filtered through silica gel with dichloromethane/ethyl acetate (3:1)
  6. customCrystallisation of the crude product from toluene

Sources & evidence

ORD record
ord-2301089622044165832758747e5fa051
Source dataset
uspto-grants-2015_01
Patent number
US08940184B2

Reaction notes

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