Ethyl chloroacetate → Ethyl 4-bromobenzofuran-2-carboxylate

HRID 1740298

反応式

HRID 1740298 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 21838105Ethyl 4-bromobenzofuran-2-carboxylate収率 70%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-98fd762db4624387b28eb07581b62cdc
出典データセット
uspto-grants-1999_10
特許番号
US05968985

関連ノート

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