Methyl iodide → 2-Bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene

HRID 1798079ノート

反応式

HRID 1798079 の反応式
[Br:1][C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[CH2:16][OH:17].[H-].[Na+].[CH3:20]I>C1COCC1>[Br:1][C:2]1[C:3]([CH2:16][O:17][CH3:20])=[CH:4][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:6][C:7]=1[O:8][CH2:9][O:10][CH3:11]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10957768[2-Bromo-3,5-bis(methoxymethoxy)phenyl]methanol

生成物 1

HCID 582927852-Bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene収率 96%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (2-bromo-3,5-bis-methoxymethoxy-phenyl)-methanol (10.2 g, 33.3 mmol) in THF (60 mL) was treated with NaH (2.67 g, 66.7 mmol) at 0° C. The resulting suspension was stirred at room temperature for 20 min. CH3I was added to the mixture and the reaction was stirred at room temperature for 1 h. The reaction was quenched with water and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=5:1) to afford the title compound (10.5 g, 96%). 1H NMR (300 MHz, CDCl3) δ 6.88 (s, 1H), 6.80 (s, 1H), 5.23 (s, 2H), 5.17 (s, 2H), 4.50 (s, 2H), 3.51 (s, 3H), 3.47 (s, 6H).

後処理

  1. stirringthe reaction was stirred at room temperature for 1 h
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-a8d8b337929e4daabfae278476c72868
出典データセット
uspto-grants-2013_01
特許番号
US08343944B2

反応ノート

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