Potassium trifluoroacetate → Ethyl 5-trifluoromethyl-6-methoxybenzo[b]thiophene-3-carboxylate

HRID 581983

반응식

HRID 581983 반응식
Br[C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:5]2[S:6][CH:7]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]=2[CH:3]=1.[F:18][C:19]([F:24])([F:23])C([O-])=O.[K+]>CN(C)C=O.C1(C)C=CC=CC=1.[Cu]I>[F:18][C:19]([F:24])([F:23])[C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:5]2[S:6][CH:7]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]=2[CH:3]=1

참가 물질

6

반응물 2

HCID 23662811Potassium trifluoroacetateHCID 53817228Ethyl 5-bromo-6-methoxybenzo[b]thiophene-3-carboxylate

생성물 1

HCID 53925736Ethyl 5-trifluoromethyl-6-methoxybenzo[b]thiophene-3-carboxylate수율 64%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

Ethyl-5-bromo-6-methoxybenzo[b]thiophene-3-carboxylate (D4) (0.81 g, 3 mmoles) in dry dimethylformamide (20 ml) and toluene (10 ml) was treated with potassium trifluoroacetate (0.78 g, 6 mmoles) and copper (I) iodide (0.98 g, 6 mmoles). The mixture was heated under reflux for 1 hr using a Dean-Stark trap to collect the toluene. The mixture was cooled and poured into water (150 ml) and extracted with diethyl ether. The resulting emulsion was filtered through kieselguhr. The combined organic extracts were washed several times with water then dried (Na2SO4). Flash chromatography on TLC silica gel eluting with dichloromethane/60-80 petrol ether 1:1 gave the title compound (D6) (0.5 g, 64%)

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. customto collect the toluene
  4. temperatureThe mixture was cooled
  5. additionpoured into water (150 ml)
  6. extractionextracted with diethyl ether
  7. filtrationThe resulting emulsion was filtered through kieselguhr
  8. washThe combined organic extracts were washed several times with water
  9. dry with materialthen dried (Na2SO4)

출처 및 근거

ORD 기록
ord-8f7003c0a7184667a2fb0c32d57f3ebe
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922733

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