Methanol → 5-Ethynyl-2-methoxybenzonitrile

HRID 2240941Notes

Reaction equation

HRID 2240941 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][Si](C)(C)C)=[CH:6][C:3]=1[C:4]#[N:5].CO.[C:18](=O)([O-])[O-:19].[Cs+].[Cs+]>C(Cl)Cl.C(OCC)C>[C:10]([C:7]1[CH:8]=[CH:9][C:2]([O:19][CH3:18])=[C:3]([CH:6]=1)[C:4]#[N:5])#[CH:11]

Participants

6

Reactant 3

HCID 887MethanolHCID 10796Cesium carbonateHCID 593053312-Fluoro-5-((trimethylsilyl)ethynyl)benzonitrile

Product 1

HCID 534292965-Ethynyl-2-methoxybenzonitrileYield 69.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-Fluoro-5-trimethylsilanylethynyl-benzonitrile (0.935 g, 4.3 mmol), in dry methylene chloride (10 mL) and methanol (10 mL) was added cesium carbonate (1.7 g, 5.2 mmol) and stirred for 2 h under a nitrogen atmosphere. The mixture was diluted with diethyl ether (100 mL), and partitioned between diethyl ether and H2O (100 mL), and the aqueous layer was extracted with diethyl ether (50 mL), washed with brine and dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography (20-30% ethyl acetate/petroleum ether) gave the title compound as a tan solid (0.468 g, 69%), identified by NMR and mass spectral analyses. Mp: 100-101° C. MS (EI+): 157 (M+).

Workup

  1. custompartitioned between diethyl ether and H2O (100 mL)
  2. extractionthe aqueous layer was extracted with diethyl ether (50 mL)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (20-30% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-1c26da37cfb643798614632de82e66c7
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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