Acetonitrile → 2-Methoxybenzonitrile

HRID 1160661Notes

Reaction equation

HRID 1160661 reaction equation
S1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.[C:9]([O-:12])([O-])=O.[Na+].[Na+].[CH2:15](Cl)Cl.[C:18](#[N:20])[CH3:19]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][O:12][C:9]1[CH:5]=[CH:4][CH:3]=[CH:2][C:19]=1[C:18]#[N:20]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acid

Product 1

HCID 810862-MethoxybenzonitrileYield 55%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of compound 3 (237 mg, 1.00 mmol), 3-thiophene boronic acid (128 mg, 1.00 mmol), Pd(PPh3)4 (58 mg, 0.05 mmol, 5 mol %) and aqueous Na2CO3 (0.4 M, 5 mL, 2.00 mmol) in acetonitrile (5 mL) was heated to reflux for 75 Min. After cooling to RT, CH2Cl2 (10 mL) was added and the phases were separated. The aqueous phase was extracted with CH2Cl2 (2×10 mL), and the combined organic extracts were dried over MgSO4 and concentrated in vacuo. Chromatography over silica (EtOAc in hexanes, 0-20%) afforded compound 4 (132 mg, 55%) as a yellow oil. LC/MS (10-99%) m/z: 241, retention time: 3.61 min. 1H-NMR (400 MHz, DMSO): δ 7.98 (s, 1H), 7.65 (m, 1H), 7.57 (m, 1H), 7.17 (m, 1H), 2.86 (s, 6H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 75 Min
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with CH2Cl2 (2×10 mL)
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fd711871c664ee59ae09e8e707f9ad7
Source dataset
uspto-grants-2010_10
Patent number
US07816529B2

Reaction notes

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