Methyl chloroacetate → 7-Bromo-5-fluorobenzofuran-2-carboxylic acid

HRID 383847

반응식

HRID 383847 반응식
Cl[CH2:2][C:3]([O:5]C)=[O:4].[Br:7][C:8]1[C:9]([OH:17])=[C:10]([CH:13]=[C:14]([F:16])[CH:15]=1)[CH:11]=O.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>O1CCCC1.O>[Br:7][C:8]1[C:9]2[O:17][C:2]([C:3]([OH:5])=[O:4])=[CH:11][C:10]=2[CH:13]=[C:14]([F:16])[CH:15]=1

참가 물질

7

반응물 4

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 231489553-Bromo-5-fluoro-2-hydroxybenzaldehyde

생성물 1

HCID 179827017-Bromo-5-fluorobenzofuran-2-carboxylic acid수율 63%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
130 °C

실험 절차

Methyl chloroacetate (7.6 mL, 86.8 mmol) was added to a mixture of 3-bromo-5-fluoro-2-hydroxy-benzaldehyde (9.5 g, 43.4 mmol), tetra-N-butyl-ammonium iodide (1.6 g, 4.34 mmol) and anhydrous potassium carbonate (24 g, 174 mmol). The reaction mixture was heated at 130° C. for 4 h, cooled to 0° C., diluted with tetrahydrofuran (100 mL) and then potassium hydroxide (17 g, 303 mmol) in water (100 mL). The mixture was stirred at rt for 18 h and then, concentrated under reduced pressure. The residue was acidified with HCl and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; toluene/EtOAc, 40/1) to give 7.0 g (63%) of the product.

후처리

  1. temperaturecooled to 0° C.
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude compound was purified by flash chromatography (SiO2; toluene/EtOAc, 40/1)

출처 및 근거

ORD 기록
ord-ad46f0e3149443759274e90b78c14389
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367676B2

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