Methyl Ethyl Ketone → Ethyl (5-bromobenzofuran)-2-carboxylate

HRID 902017

反応式

HRID 902017 の反応式
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.C([C:13](CC)([C:18]([O-:20])=[O:19])C(OBr)=O)C.C(=O)([O-])[O-].[K+].[K+].[CH2:29](C(C)=O)[CH3:30]>>[CH2:29]([O:20][C:18]([C:13]1[O:10][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=2[CH:7]=1)=[O:19])[CH3:30]

参加物

5

反応物 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 86590788Bromo diethylmalonate

生成物 1

HCID 735184Ethyl (5-bromobenzofuran)-2-carboxylate収率 78%

実験手順

A solution of 5-bromo-salicylaldehyde (5.0 g, 25 mmol) and bromo diethylmalonate (8.9 g, 37 mmol) in methyl ethyl ketone (50 mL) is treated with potassium carbonate (6.8 g, 50 mmol) and heated to reflux. The reaction is stirred over 3 days at reflux. The reaction is then concentrated to a crude solid that is purified by silica gel column chromatography (9:1 hexane/EtOAc) to afford 5.2 g (78%) of the desired product. 1H NMR (CDCl3) 7.81 (d, 1H), 7.26-7.55 (m, 3H), 4.44 (q, 2H), 1.42 (t, 3H).

後処理

  1. temperatureheated to reflux
  2. temperatureat reflux
  3. concentrationThe reaction is then concentrated to a crude solid
  4. customthat is purified by silica gel column chromatography (9:1 hexane/EtOAc)

出典と根拠

ORDレコード
ord-dcd1e3fcb5a746e995bd0fae885d2464
出典データセット
uspto-grants-2008_04
特許番号
US07365066B2

関連ノート

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