Iodine → HCID 15920607, compound

HRID 420419Notes

Reaction equation

HRID 420419 reaction equation
[Mg].II.Br[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=1[CH3:13].[CH3:14][O:15][B:16](OC)[O:17][CH3:18]>C1COCC1.CCOCC>[CH3:14][O:15][B:16]([O:17][CH3:18])[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=1[CH3:13]

Participants

7

Reactant 4

HCID 807IodineHCID 8470Trimethyl borateHCID 684732-BromomesityleneHCID 5462224Magnesium

Product 1

HCID 15920607HCID 15920607, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

To a stirred solution of activated magnesium flakes (3.11 g, 0.128 mol) and a crystal of iodine, 2-bromomesitylene (23.40 g, 0.118 mol) in THF (80 cm3) was added dropwise at room temperature. The reaction was allowed to reflux for 3 hours. After the reaction mixture was cooled, it was added dropwise to an ether solution (80 cm3) of trimethoxyborane (26 cm3, 0.229 mol) at −15° C. The reaction stirred at −15° C. for 3 hours and then was warmed up to room temperature and left to stir overnight. The solution was then filtered under argon and the precipitated salts were washed with dry pentane (20 cm3). The filtrates were combined, concentrated and distilled under vacuum to give the desired dimethoxymesitylborane. 1H NMR (200 MHz, CDCl3) δ 2.28 (s, 6H), 2.30 (s, 3H), 3.58 (s, 6H), 6.84 (s, 2H).

Workup

  1. temperatureto reflux for 3 hours
  2. temperatureAfter the reaction mixture was cooled
  3. temperaturewas warmed up to room temperature
  4. waitleft
  5. stirringto stir overnight
  6. filtrationThe solution was then filtered under argon
  7. washthe precipitated salts were washed with dry pentane (20 cm3)
  8. concentrationconcentrated
  9. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-022ebe7c70e2498db1d4cfce8c26c4af
Source dataset
uspto-grants-2012_01
Patent number
US08097348B2

Reaction notes

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