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

HRID 1511226ノート

反応式

HRID 1511226 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f5d4082b3cb743b3a3951171623f0b26
出典データセット
uspto-grants-2012_07
特許番号
US08212011B2

反応ノート

読み込み中…