Ethyl chloroacetate → Ethyl 4-bromobenzofuran-2-carboxylate

HRID 1740298

반응식

HRID 1740298 반응식
[Br:1][C:2]1[C:7]([CH:8]=O)=[C:6]([OH:10])[CH:5]=[CH:4][CH:3]=1.Cl[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[C:7]2[CH:8]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 119547682-Bromo-6-hydroxybenzaldehyde

생성물 1

HCID 21838105Ethyl 4-bromobenzofuran-2-carboxylate수율 70%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

A mixture of 6-bromo-2-hydroxybenzaldehyde (4.48 g), ethyl chloroacetate (3.55 g) and powdered potassium carbonate (6.16 g) in N,N-dimethylformamide (56 ml) was stirred at 120° C. for one hour. Insoluble materials were filtered off and the solvent was removed under reduced pressure. Ethyl acetate and water were added to the residue, and the mixture was acidified by hydrochloric acid solution. The layers were separated and the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane and toluene (1:1) to afford 4-bromo-2-ethoxycarbonylbenzofuran (4.20 g).

후처리

  1. filtrationInsoluble materials were filtered off
  2. customthe solvent was removed under reduced pressure
  3. additionEthyl acetate and water were added to the residue
  4. customThe layers were separated
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and toluene (1:1)

출처 및 근거

ORD 기록
ord-98fd762db4624387b28eb07581b62cdc
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968985

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