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

HRID 18828

반응식

HRID 18828 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 302826Ethyl 2-(2-chlorophenoxy)acetate수율 97.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b29967885a46478f8ec56bcdaffb4281
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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