Potassium Iodide → HCID 23497798, compound

HRID 1837145Notes

Reaction equation

HRID 1837145 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[NH2:14].Br[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(#N)C>[C:23]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][NH:14][C:13]1[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:11]([O:10][CH3:9])[CH:12]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 227703,4-DimethoxyanilineHCID 2633651-(Bromomethyl)-2-phenylbenzene

Product 1

HCID 23497798HCID 23497798, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (1.38 g, 10 mmol), catalytic amount of potassium iodide, and 3,4-dimethoxyaniline (1.53 g 10 mmol) were added to a solution of 2-(bromomethyl)biphenyl (1.83 mL, 10 mmol) in acetonitrile (200 mL). The reaction mixture was heated and stirred at 80° C. for 18 hours, then was cooled to room temperature. The solid was filtered and the filtrate concentrated to dryness. Purification by silica gel column chromatography using 20% ethyl acetate in hexanes as the eluant afforded the pure product (1.04 g). MH+320: 1H (CDCl3) δ 3.77 (3H, s), 3.78 (3H, s), 4.21 (2H, s), 6.05 (1H, dd, J=8, 3), 6.14 (1H, m) 6.67 (1H, d, J=8), 7.28-7.42 (8H, m), 7.54 (1H, m).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturewas cooled to room temperature
  3. filtrationThe solid was filtered
  4. concentrationthe filtrate concentrated to dryness
  5. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-ac0232f9362f48fa9256d25ee00b1d1a
Source dataset
uspto-grants-2004_08
Patent number
US06780883B2

Reaction notes

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