Sodium Iodide → HCID 19791786, compound

HRID 450504Notes

Reaction equation

HRID 450504 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N-:15]=[N+:16]=[N-:17].[Na+].[I-].[Na+]>CS(C)=O>[C:4]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][N:15]=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 2633651-(Bromomethyl)-2-phenylbenzene

Product 1

HCID 19791786HCID 19791786, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-(bromomethyl)biphenyl (1.5 g, 6 mmol) in DMSO (15 mL) was added sodium azide (0.59 g, 9 mmol) and a catalytic amount of sodium iodide. The mixture was stirred at room temperature for 2 days. After concentration under reduced pressure, the residue was diluted with ethyl acetate. The organic layer was washed with brine (2×60 mL), dried on sodium sulphate and after filtration was evaporated to dryness to give the title compound as an oil (1.1 g, 87%). 1H NMR (300 MHz, CDCl3, ppm) δ: 7.56−7.38 (m, 9H), 4.37 (s, 2H).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe organic layer was washed with brine (2×60 mL)
  4. customdried on sodium sulphate
  5. filtrationafter filtration
  6. customwas evaporated to dryness

Sources & evidence

ORD record
ord-cf2de1a6cedc4a8bb612f45bbafb84c7
Source dataset
uspto-grants-2013_07
Patent number
US08486977B2

Reaction notes

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