4-Iodo-N-methoxy-N-methyl-benzamide → 1-(4-Iodophenyl)-2-(4-methoxyphenyl)ethanone

HRID 534244Notes

Reaction equation

HRID 534244 reaction equation
[I:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([CH2:20][Mg]Cl)=[CH:18][CH:17]=1>>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:7])[CH2:20][C:19]2[CH:23]=[CH:24][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 54617564-Iodo-N-methoxy-N-methyl-benzamideHCID 178490607HCID 178490607, compound

Product 1

HCID 433382141-(4-Iodophenyl)-2-(4-methoxyphenyl)ethanoneYield 65.5%

Conditions

Temperature
0 °C

Procedure

4-Iodo-N-methoxy-N-methylbenzamide (3.4 g, 11.7 mmol) was added dropwise over 5 min (internal temperature kept below 5° C.) to a vigorously stirring solution of (4-methoxybenzyl)magnesium chloride (52 mL, 0.25M in 2-MeTHF, 13 mmol) at 0° C. under N2. After 10 min, a white precipitate was observed. After 5 hours of vigorous stirring at 0° C., the reaction was quenched with 1N HCl (50 mL). When the internal temperature returned to 0° C., the reaction was filtered, and the filter cake was washed with ethyl acetate (50 mL) (Note #1). The filter cake was dried under vacuum to give 2.7 g of 1-(4-iodophenyl)-2-(4-methoxyphenyl)ethanone as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.92 (d, 2H), 7.78 (d, 2H), 7.16 (d, 2H), 6.87 (d, 2H), 4.28 (s, 2H), 3.72 (s, 3H).

Workup

  1. customthe reaction was quenched with 1N HCl (50 mL)
  2. customreturned to 0° C.
  3. filtrationthe reaction was filtered
  4. washthe filter cake was washed with ethyl acetate (50 mL) (Note #1)
  5. customThe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-b4fe254f91a84f089b25552e4956abc2
Source dataset
uspto-grants-2014_10
Patent number
US08853423B2

Reaction notes

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