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

HRID 1798057ノート

反応式

HRID 1798057 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.CCOCC>[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

6

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 70%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2-bromo-3,5-bis-methoxymethoxy-phenyl)-methanol (7.68 g, 24.94 mmol) in THF (50 mL) was added NaH at 0° C. The mixture was stirred at room temperature for 20 minutes then MeI (7.84 mL) was added and the resulting mixture was stirred at room temperature for 2 hours. The mixture was diluted with ether (50 mL), filtered through a pad of celite and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 2-bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene (5.66 g, 70%). 1H NMR (400 MHz, CDCl3δ 6.90 (s, 1H), 6.80 (s, 1H), 6.77 (s, 1H), 5.25 (s, 2H), 5.20 (s, 2H), 4.50 (s, 23.77 (s, 3H), 3.40 (s, 6H).

後処理

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel flash column chromatography

出典と根拠

ORDレコード
ord-e3c95b5787a74fe59dc06643bd6ac7e0
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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