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

HRID 581983

反応式

HRID 581983 の反応式
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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

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%)

後処理

  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)

出典と根拠

ORDレコード
ord-8f7003c0a7184667a2fb0c32d57f3ebe
出典データセット
uspto-grants-1999_07
特許番号
US05922733

関連ノート

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