Borane;tetrahydrofuran → 5-(Aminomethyl)-2-iodophenol

HRID 2236475Notes

Reaction equation

HRID 2236475 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[I:10])[C:5]#[N:6].B.C1COCC1>C1COCC1>[NH2:6][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([I:10])=[C:2]([OH:1])[CH:3]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 109446813-Hydroxy-4-iodobenzonitrile

Product 1

HCID 426255945-(Aminomethyl)-2-iodophenolYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-Hydroxy-4-iodo-benzonitrile (300 mg, 1.22 mmol) in THF (5 mL) is added BH3.THF (10 mL, 1 M solution in THF, 10 mmol) under N2. The mixture is then allowed to stir at room temperature for 24 hours. The reaction is quenched with 6N HCl. THF is removed and the aqueous layer is neutralized with ammonium hydroxide to pH 9. The mixture is extracted with CHCl3/MeOH (9:1). The organic layer dried and evaporated and the residue is chromatographed to provide the desired product (60 mg, 20%). MS (ESI): 250 (M+1)−1.

Workup

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

Sources & evidence

ORD record
ord-1951e9d2445542689ba60926485ebedd
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…