Sodium Carbonate → Methyl 5-(4-fluorophenyl)thiophene-2-carboxylate

HRID 1835460노트

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HRID 1835460 반응식
Br[C:2]1[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:6]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:10][O:9][C:7]([C:4]1[S:3][C:2]([C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=2)=[CH:6][CH:5]=1)=[O:8]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 605713Methyl 5-bromothiophene-2-carboxylate

생성물 1

HCID 3263823Methyl 5-(4-fluorophenyl)thiophene-2-carboxylate수율 98.3%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

To a suspension of 2-bromo-5-methoxycarbonylthiophene (1.11 g), 4-fluorophenylboronic acid (0.91 g) and tetrakis(triphenylphosphine)palladium (289 mg) in 1,2-dimethoxyethane (10 ml) was added aqueous solution of sodium carbonate (2M, 6.5 ml) followed by stirring at 80° C. for 6 hours. The mixture was diluted with dichloromethane and washed with water and brine. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by a silica gel column chromatography eluting with 30% dichloromethane in n-hexane to give 2-methoxycarbonyl-5-(4-fluorophenyl)thiophene (1.16 g, 98.3%).

후처리

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by a silica gel column chromatography
  5. washeluting with 30% dichloromethane in n-hexane

출처 및 근거

ORD 기록
ord-a3f5d724c0134cb68ca294b128eaead6
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06770667B1

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