Ethyl bromoacetate → Ethyl (2-bromo-3-formylphenoxy)acetate

HRID 561836노트

반응식

HRID 561836 반응식
[Br:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C>[Br:1][C:2]1[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 37146742-Bromo-3-hydroxybenzaldehyde

생성물 1

HCID 59515317Ethyl (2-bromo-3-formylphenoxy)acetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-bromo-3-hydroxybenzaldehyde (1 eq.) in DMF (0.4 M) was added cesium carbonate (1.2 eq.) and ethyl bromoacetate (1 eq.). The resulting suspension was stirred at RT for 16 h. The reaction mixture was quenched with water and extracted with EtOAc. The combined organic extracts were washed with water and brine. Drying over MgSO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a red oil. Purification by way of column chromatography (SiO2, 5:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc) afforded the title compound.

후처리

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialDrying over MgSO4, filtration and concentration of the filtrate in vacuo
  5. customafforded the crude product as a red oil
  6. customPurification by way of column chromatography (SiO2, 5:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc)

출처 및 근거

ORD 기록
ord-05babb2afc18419a9894d817c93427e8
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063105B2

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