Boron tribromide → Ethyl 5-hydroxybenzofuran-2-carboxylate

HRID 493168

反応式

HRID 493168 の反応式
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 5212832-Benzofurancarboxylic acid, 5-methoxy-, ethyl ester

生成物 1

HCID 22228632Ethyl 5-hydroxybenzofuran-2-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

The above prepared 5-methoxy-benzofuran-2-carboxylic acid ethyl ester (8.10 g, 36.8 mmol) was dissolved in 250 mL of CH2Cl2, cooled to 0° C., and treated with BBr3 (73.6 mL of 1M solution in CH2Cl2, 2 eq.). After 2 h, the reaction mixture was carefully poured onto crashed ice, twofold extracted with CH2Cl2, washed with brine, dried over magnesium sulfate, and evaporated to dryness. Ensuing flash chromatography (SiO2, hexane/AcOEt=8/2) delivered then 5.63 g of the title compound as off-white crystals.

後処理

  1. additionthe reaction mixture was carefully poured
  2. extractiontwofold extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-fae4dd29020d4c56ba37b03c148f2d48
出典データセット
uspto-grants-2009_05
特許番号
US07534788B2

関連ノート

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