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Water → 1-(4-Fluorophenyl)prop-2-yn-1-ol

HRID 1062587
Notes
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Reaction equation

HRID 1062587 reaction equation
FC1C=C(C=CC=1F)CN1C(=[O:16])C2C(=CC=C(I)C=2)N(C)C1=O.C(N(C(C)C)CC)(C)C.[F:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][C:41]#[CH:42])=[CH:36][CH:35]=1.O>CN(C=O)C.[Cu]I>[F:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]([OH:16])[C:41]#[CH:42])=[CH:36][CH:35]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 105586681-Fluoro-4-prop-2-ynyl-benzeneHCID 222818613-(3,4-Difluoro-benzyl)-6-iodo-1-methyl-1H-quinazoline-2,4-dione

Product 1

HCID 112751051-(4-Fluorophenyl)prop-2-yn-1-ol

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To 0.5 g (1.06 mmol) 3-(3,4-Difluoro-benzyl)-6-iodo-1-methyl-1H-quinazoline-2,4-dione and 0.52 g (4.2 mmol) di-isopropyl ethylamine in 15 ml DMF is added bis-triphenylphosphine palladium di-chloride (catalytic) followed by CuI (catalytic). 0.15 g (1.3 mmol) 1-fluoro-4-prop-2-ynyl-benzene is added and the mixture is heated to 70° C. for 6 hours. The mixture is allowed to cool to room temperature and stir overnight. Water is added and the mixture stirred 30 minutes. Filtered and triturated solid in hot EtOAc and filtered. Purified by flash chromatography (EtOAc/hexane eluent).

Workup

  1. temperatureto cool to room temperature
  2. stirringthe mixture stirred 30 minutes
  3. filtrationFiltered
  4. customtriturated solid in hot EtOAc
  5. filtrationfiltered
  6. customPurified by flash chromatography (EtOAc/hexane eluent)

Sources & evidence

ORD record
ord-adaec6dc47264deeb65b987101823425
Source dataset
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06962922B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes