Iodine → HCID 12115481, compound

HRID 2373332Notes

Reaction equation

HRID 2373332 reaction equation
[Mg].II.C(Br)[CH2:5][CH:6]([CH3:8])[CH3:7].N[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].[Cl-].[NH4+:21].[C:22](OCC)(=O)C>C(OCC)C>[OH:13][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:21])([CH3:22])[CH2:11][CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

8

Reactant 6

HCID 807IodineHCID 78911-Bromo-3-methylbutaneHCID 8857Ethyl AcetateHCID 11952PhenacylamineHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 12115481HCID 12115481, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Magnesium (960 mg, 40 mmol) and then a catalytic amount of iodine were added to diethyl ether (15 ml), followed by slowly adding thereto isoamyl bromide (6.04 g, 40 mmol) with refluxing, and the resulting mixture was stirred at reflux temperature for 30 minutes and then at room temperature for 30 minutes. To the resulting solution was added 2-aminoacetophenone (1.8 g, 13.3 mmol) under ice-cooling, followed by stirring at room temperature for 3 hours. Ammonium chloride was added thereto and the resulting mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure to obtain 2.7 g of 2-(1-hydroxy-1,4-dimethylpentyl)aniline.

Workup

  1. additionby slowly adding
  2. temperatureat reflux temperature for 30 minutes
  3. temperaturecooling
  4. stirringby stirring at room temperature for 3 hours
  5. washwashed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e6448331eb44411a88d862ff124a4e07
Source dataset
uspto-grants-2008_12
Patent number
US07459477B2

Reaction notes

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