Borane;tetrahydrofuran → 3-(Aminomethyl)-4-iodophenol

HRID 2236472Notes

Reaction equation

HRID 2236472 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH:9]=1)[C:7]#[N:8].B.C1COCC1>C1COCC1>[NH2:8][CH2:7][C:6]1[CH:9]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=1[I:10]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 686960525-Hydroxy-2-iodobenzonitrile

Product 1

HCID 593000293-(Aminomethyl)-4-iodophenolYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-Hydroxy-2-iodo-benzonitrile (245 mg, 1 mmol) in THF (3 mL) is added BH3.THF (6 mL, 1 M solution in THF) under N2. The mixture is then allowed to stir at room temperature for 24 hours. The reaction is then quenched with 6N HCl. THF is then removed and the aqueous layer is then neutralized with ammonium hydroxide to pH 9. The mixture is then extracted with CHCl3/MeOH (9:1). The organic layer dried and evaporated and the residue is chromatographed to provide the desired product (80 mg, 32%).

Workup

  1. customThe reaction is then quenched with 6N HCl
  2. customTHF is then removed
  3. extractionThe mixture is then extracted with CHCl3/MeOH (9:1)
  4. customThe organic layer dried
  5. customevaporated
  6. customthe residue is chromatographed

Sources & evidence

ORD record
ord-1e0c066abd264201af02fb95b0cb6613
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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