Chloromethyl Methyl Ether → HCID 42625597, compound

HRID 2236476Notes

Reaction equation

HRID 2236476 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[I:10])[C:5]#[N:6].[CH2:11](Cl)[O:12][CH3:13].[H-].[Na+]>CN(C)C=O>[I:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[O:1][CH2:11][O:12][CH3:13]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 109446813-Hydroxy-4-iodobenzonitrile

Product 1

HCID 42625597HCID 42625597, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-hydroxy-4-iodobenzonitrile (500 mg, 2.04 mmol) and MOMCl (350 mg, 4.37 mmol) were dissolved in anhydrous N,N-dimethylformamide (5 mL) and cooled to 0° C. NaH (100 mg, 60% suspension in mineral oil, 2.5 mmol) is then added. The resulting mixture is allowed to stir at room temperature for 1 h before TLC analysis suggested the consumption of the starting iodide. Ether is then added and washed with H2O (3×20 mL) and brine. After drying over Na2SO4, the ether is removed and the residue is purified through chromatography to afford the desired MOM ether (570 mg, 96%). 1H NMR (300 MHz, CDCl3) δ 7.90 (1H, d, J=8.01 Hz), 7.32 (1H, d, J=1.7 Hz), 7.03 (1H, dd, J=8.01 and 1.71 Hz), 5.27 (2H, s), 3.51 (3H, s).

Workup

  1. customthe consumption of the starting iodide
  2. additionEther is then added
  3. washwashed with H2O (3×20 mL) and brine
  4. dry with materialAfter drying over Na2SO4
  5. customthe ether is removed
  6. customthe residue is purified through chromatography
  7. customto afford the desired MOM ether (570 mg, 96%)

Sources & evidence

ORD record
ord-a8e933c3899f4e33a0349c975d6cafd3
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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