4-Iodoaniline → HCID 67059834, compound

HRID 601451Notes

Reaction equation

HRID 601451 reaction equation
[CH3:1][C@@H:2]([CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.I[C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>>[CH3:1][C@@H:2]([CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:21]2[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 108934-IodoanilineHCID 67059828HCID 67059828, compound

Product 1

HCID 67059834HCID 67059834, compoundYield 67.4%

Procedure

A mixture of 4-[(3S)-3,7-dimethyl-6-octenyl]phenylboronic acid (5.00 g, 19.2 mmol), 4-iodoaniline (2.79 g, 12.75 mmol), and a quaternary ammonium salt (Aliquat 336, 1.3 g) was degased three times with nitrogen before 100 mL of dry toluene was added. This step was followed by addition of tetrakis(triphenylphosphine)palladium (1.46 g) and aqueous sodium carbonate (1 M, 60 mL, deaerated for 2 hours) under nitrogen. The mixture was stirred vigorously and heated under reflux for 20 hours. The organic phase of the resulting reaction mixture was filtered through a thin layer of Celite® and evaporated to dryness to give 3.09 g of crude material. The crude material was purified by chromatography on silica gel (ethyl acetate:hexanes) to yield 4-[(3S)-3,7-dimethyl-6-octenyl]-4′-aminobiphenyl as a yellow oil (2.64 g, 8.59 mmol, 67.4% yield).

Workup

  1. customa quaternary ammonium salt (Aliquat 336, 1.3 g) was degased three times with nitrogen before 100 mL of dry toluene
  2. additionwas added
  3. additionThis step was followed by addition of tetrakis(triphenylphosphine)palladium (1.46 g) and aqueous sodium carbonate (1 M, 60 mL, deaerated for 2 hours) under nitrogen
  4. temperatureheated
  5. temperatureunder reflux for 20 hours
  6. customThe organic phase of the resulting reaction mixture
  7. filtrationwas filtered through a thin layer of Celite®
  8. customevaporated to dryness
  9. customto give 3.09 g of crude material
  10. customThe crude material was purified by chromatography on silica gel (ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-f9547898a2e4491c819784f848246684
Source dataset
uspto-grants-2011_03
Patent number
US07902363B2

Reaction notes

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