Water → (5-Chloro-2-iodophenyl)methanamine

HRID 1058255Notes

Reaction equation

HRID 1058255 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([I:31])=[C:25]([CH:30]=1)[CH2:26][N:27]=[N+]=[N-].O>C1COCC1>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([I:31])=[C:25]([CH:30]=1)[CH2:26][NH2:27]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 18672362HCID 18672362, compound

Product 1

HCID 18672388(5-Chloro-2-iodophenyl)methanamineYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

PPh3 (1.46 g, 5.58 mmol) was added to a stirred solution of 5-chloro-2-iodobenzylazide (0.55 g, 1.86 mmol) in THF (17.5 mL), and water (3.5 mL) were combined and stirred at room temperature. After 16 hr, the mixture was warmed to 80° C. for 3 h. The reaction was then concentrated and the residue was partitioned between ether and 1N HCl. The aqueous layer was adjusted to pH=8 with NaHCO3, saturated with NaCl and then extracted into CH2Cl2. The CH2Cl2 layer was washed with brine, dried (Na2SO4) and evaporated to give 5-chloro-2-iodobenzylamine (428 mg): 1H NMR (CDCl3, 400 MHz) δ 3.83 (s, 2H), 6.95 (dd, J=2.6, 8.4 Hz, 1H), 7.40 (d, J=2.4 Hz, 1H), 7.72 (d, J=8.2 Hz, 1H).

Workup

  1. temperaturethe mixture was warmed to 80° C. for 3 h
  2. concentrationThe reaction was then concentrated
  3. customthe residue was partitioned between ether and 1N HCl
  4. extractionextracted into CH2Cl2
  5. washThe CH2Cl2 layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-9ba05b69c0c64f97a003dadc2b3be3e1
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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