Iodoethane → Ethyl 7-bromo-5-fluorobenzofuran-2-carboxylate

HRID 383848

반응식

HRID 383848 반응식
[CH2:1](I)[CH3:2].[Br:4][C:5]1[C:13]2[O:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]=2[CH:8]=[C:7]([F:17])[CH:6]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:4][C:5]1[C:13]2[O:12][C:11]([C:14]([O:16][CH2:1][CH3:2])=[O:15])=[CH:10][C:9]=2[CH:8]=[C:7]([F:17])[CH:6]=1

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 179827017-Bromo-5-fluorobenzofuran-2-carboxylic acid

생성물 1

HCID 59636759Ethyl 7-bromo-5-fluorobenzofuran-2-carboxylate수율 90.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

Ethyl iodide (4.6 ml, 57.2 mmol) was added to a mixture of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid (3.7 g, 14.3 mmol) and sodium bicarbonate (4.8 g, 57.2 mmol) in anhydrous dimethylformamide (40 mL). The mixture was heated at 55° C. for 18 h, cooled to rt, quenched with water (20 mL) and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1) to give 3.7 g (90%) of the product.

후처리

  1. temperaturecooled to rt
  2. customquenched with water (20 mL)
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1)

출처 및 근거

ORD 기록
ord-336d4b8ed6594011bc6c0c7e2af2fd21
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367676B2

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