Sodium hydride → 1-Bromo-4-methoxy-2-(methoxymethoxy)benzene

HRID 365355ノート

反応式

HRID 365355 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].[H-].[Na+].Br[CH2:14][O:15][CH3:16]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:14][O:15][CH3:16]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 134938392-Bromo-5-methoxyphenol

生成物 1

HCID 148270371-Bromo-4-methoxy-2-(methoxymethoxy)benzene収率 106.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-Bromo-2-hydroxy-4-methoxybenzene (5.00 g, 24.60 mmol) in DMF was added 60% sodium hydride (1.97 g, 49.20 mmol) at 0° C. under argon. The mixture was allowed to stir at 0° C. for 15 minutes, then 90% bromomethyl methylether (4.10 g, 29.50 mmol) was added. After stirring for 1 h at 0° C. the reaction was quenched with water. The mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent afforded the title compound as an oil (6.5 g, quantitative yield). 1H NMR (400 MHz, CDCl3) δ 7.41 (d, 2H), 6.76 (d, 1H), 6.47 (dd, 1H), 5.24 (s, 2H), 3.87 (s, 3H), 3.53 (s, 3H).

後処理

  1. stirringAfter stirring for 1 h at 0° C. the reaction
  2. customwas quenched with water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent

出典と根拠

ORDレコード
ord-0cd264c8315b4a22b5e121824522d7bb
出典データセット
uspto-grants-2000_10
特許番号
US06127371

反応ノート

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