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

HRID 902017

반응식

HRID 902017 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

HCID 735184Ethyl (5-bromobenzofuran)-2-carboxylate수율 78%

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-dcd1e3fcb5a746e995bd0fae885d2464
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365066B2

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