Diethyl Ether → Ethyl 2-(2-chlorophenoxy)acetate

HRID 18828

反応式

HRID 18828 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].CCOCC>CN(C=O)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:21]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 72452-ChlorophenolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

生成物 1

HCID 302826Ethyl 2-(2-chlorophenoxy)acetate収率 97.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-chlorophenol (2.06 mL, 19.9 mmol) in DMF (40 mL) is added potassium carbonate (3.03 g, 21.9 mmol) and ethyl bromoacetate (2.3 mL, 20.7 mmol), and the mixture is stirred at 80° C. for 18 h. Et2O is added, and the mixture is washed with water, brine, dried (MgSO4), and filtered. The filtrate is evaporated, and the residue is purified by chromatography in silica gel; elution with EtOAc:dichloromethane:hexane (10:5:85) gives 4.17 g of the product 465. 1H NMR (CDCl3) δ 7.38 (d, 1H), 7.21 (t, 1H), 6.92 (t, 1H), 6.84 (d, 1H), 4.70 (s, 2H), 4.27 (q, 2H), 1.29 (t, 3H); MS: m/z 215, 217 (M++1).

後処理

  1. washthe mixture is washed with water, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe residue is purified by chromatography in silica gel
  6. washelution with EtOAc:dichloromethane:hexane (10:5:85)

出典と根拠

ORDレコード
ord-b29967885a46478f8ec56bcdaffb4281
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

関連ノート

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