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

HRID 1511226Notes

Reaction equation

HRID 1511226 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 2 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) 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 2 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-f5d4082b3cb743b3a3951171623f0b26
Source dataset
uspto-grants-2012_07
Patent number
US08212011B2

Reaction notes

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