Potassium Carbonate → Ethyl 5-bromo-4-methylbenzofuran-2-carboxylate

HRID 2036045노트

반응식

HRID 2036045 반응식
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([C:7]([OH:10])=[CH:8][CH:9]=1)[CH:5]=O.C(=O)([O-])[O-].[K+].[K+].[C:18]([O:21][CH2:22][CH3:23])(=[O:20])[CH3:19].CCCCCC>CN(C=O)C>[CH2:22]([O:21][C:18]([C:19]1[O:10][C:7]2[CH:8]=[CH:9][C:2]([Br:1])=[C:3]([CH3:11])[C:4]=2[CH:5]=1)=[O:20])[CH3:23]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 156998303-Bromo-6-hydroxy-2-methylbenzaldehydeHCID 21226206Ethyl acetate hexane

생성물 1

HCID 67200885Ethyl 5-bromo-4-methylbenzofuran-2-carboxylate수율 69.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a solution of 3-Bromo-6-hydroxy-2-methyl-benzaldehyde (6.8 g, 0.032 mol)) in anhydrous DMF (50 ml) was added potassium carbonate (13.1 g, 0.095 mol) and cooled to 0° C. Bromo ethyl acetate (7.1 ml, 0.063 mol) was added slowly. The reaction mixture was stirred for one hour at 0° C. The completion of the reaction was confirmed by TLC. The reaction mixture was then heated to 100° C. and maintained for 2 hours. After cooling to room temperature, ice water (250 ml) was added and the mixture was stirred for 20 minutes. The solid separated was filtered, washed with water (100 ml) and dried under vacuum, to get crude product. Column chromatography using 2/5 ethyl acetate/hexane yielded 5-Bromo-4-methyl-benzofuran-2-carboxylic acid ethyl ester (6.2 g, 69.6%)

후처리

  1. temperatureThe reaction mixture was then heated to 100° C.
  2. temperaturemaintained for 2 hours
  3. temperatureAfter cooling to room temperature
  4. stirringthe mixture was stirred for 20 minutes
  5. customThe solid separated
  6. filtrationwas filtered
  7. washwashed with water (100 ml)
  8. customdried under vacuum
  9. customto get crude product

출처 및 근거

ORD 기록
ord-33df53f91abf4461ab2a4da271676688
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575161B2

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