Potassium Carbonate → 1-[(4-Ethynylphenoxy)methyl]-3-fluorobenzene

HRID 2184353Notes

Reaction equation

HRID 2184353 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si](C)(C)C)=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22476627({4-[(3-Fluorophenyl)methoxy]phenyl}ethynyl)(trimethyl)silane

Product 1

HCID 224766251-[(4-Ethynylphenoxy)methyl]-3-fluorobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.06 g (6.9 mmol) of [4-(3-fluoro-benzyloxy)-phenylethynyl]-trimethyl-silane in 35 ml methanol is treated with 95 mg (0.69 mmol) of solid potassium carbonate. The mixture is stirred at RT for 3 h, concentrated and treated with saturated aqueous sodium hydrogencarbonate. The compound is extracted three times with dichloromethane, dried over magnesium sulfate and concentrated to yield 1.53 g (98%) of a slightly brown oil. MS (neg.ions): m/e=225.4 (M−H).

Workup

  1. concentrationconcentrated
  2. additiontreated with saturated aqueous sodium hydrogencarbonate
  3. extractionThe compound is extracted three times with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto yield 1.53 g (98%) of a slightly brown oil

Sources & evidence

ORD record
ord-bc4eb899c74b4bd2ab2f8e5febe080d8
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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