Sodium Iodide → 2-(Iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 2390898Notes

Reaction equation

HRID 2390898 reaction equation
Br[CH2:2][B:3]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])([CH3:10])[O:4]1.[I-:12].[Na+]>CC(C)=O>[I:12][CH2:2][B:3]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])([CH3:10])[O:4]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 109551102-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 109015942-(Iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 98.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the mixture of 2-(bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.0 g, 8.3 mmol) synthesized in Production Example 2 and acetone (17 ml), sodium iodide (1.9 g, 13 mmol) was added at room temperature, and the obtained reaction mixture was stirred at room temperature for 2 hours. Impurities were removed by filtration, and the solvents were evaporated under reduced pressure from the filtrate. Hexane was added to the obtained residue, and insoluble matter was removed by filtration. The solvents were evaporated under reduced pressure from the filtrate, thereby obtaining the entitled compound (2.2 g, 97%).

Workup

  1. additionwas added at room temperature
  2. customthe obtained reaction mixture
  3. customImpurities were removed by filtration
  4. customthe solvents were evaporated under reduced pressure from the filtrate
  5. additionHexane was added to the obtained residue, and insoluble matter
  6. customwas removed by filtration
  7. customThe solvents were evaporated under reduced pressure from the filtrate

Sources & evidence

ORD record
ord-a063da5f07224eab8d34d60cc280de6a
Source dataset
uspto-grants-2012_09
Patent number
US08273885B2

Reaction notes

Loading…