Iodine → 2-Iodo-1,3-bis(methoxymethoxy)benzene

HRID 2272781Notes

Reaction equation

HRID 2272781 reaction equation
C([Li])CCC.[CH3:6][O:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][O:18][CH3:19])[CH:11]=1.[I:20]I>C1COCC1>[I:20][C:11]1[C:12]([O:16][CH2:17][O:18][CH3:19])=[CH:13][CH:14]=[CH:15][C:10]=1[O:9][CH2:8][O:7][CH3:6]

Participants

5

Reactant 3

HCID 807IodineHCID 122226821,3-Bis(methoxymethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 251387872-Iodo-1,3-bis(methoxymethoxy)benzeneYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (2.5 M in hexanes, 0.22 mL, 0.56 mmol) was added to a solution of 12 (100 mg, 0.50 mmol) in anhydrous THF (790 μL) at 0° C. After 5 minutes, iodine (141 mg, 0.56 mmol) in anhydrous THF (320 μL) was added. After two hours at room temperature, the reaction was quenched via dropwise addition of MeOH and the solvent was concentrated. Water (5 mL) was added and the solution was extracted with EtOAc (3×10 mL). Combined organics were washed with saturated aqueous Na2S2O3, saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated to afford 15 as a brown oil (129 mg, 79%): 1H NMR (CDCl3, 100 MHz) δ 7.25-7.18 (m, 1H), 6.79-6.71 (m, 2H), 5.27 (s, 2H), 5.18 (s, 2H), 3.54 (s, 3H), 3.50 (s, 3H); IR (film) νmax 2953, 2924, 2853, 1458, 1377 cm−1.

Workup

  1. waitAfter two hours at room temperature
  2. customthe reaction was quenched via dropwise addition of MeOH
  3. concentrationthe solvent was concentrated
  4. additionWater (5 mL) was added
  5. extractionthe solution was extracted with EtOAc (3×10 mL)
  6. washCombined organics were washed with saturated aqueous Na2S2O3, saturated aqueous NaCl
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6275d5734b7b4c3da2fe02fdc01e74df
Source dataset
uspto-grants-2015_09
Patent number
US09120774B2

Reaction notes

Loading…