Hydrochloric Acid → 5-(4-Methoxyphenyl)thiophene-2-carbonitrile

HRID 2121299노트

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HRID 2121299 반응식
Br[C:2]1[S:3][C:4]([C:7]#[N:8])=[CH:5][CH:6]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>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.C(COC)OC>[C:7]([C:4]1[S:3][C:2]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[CH:6][CH:5]=1)#[N:8]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 35950595-Bromothiophene-2-carbonitrile

생성물 1

HCID 154458915-(4-Methoxyphenyl)thiophene-2-carbonitrile수율 80.2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of 2-bromo-5-cyanothiophene (4.9 g), 4-methoxyphenyl boronic acid (4.7 g), 2M aqueous sodium carbonate solution (80 cm3), tetrakis(triphenylphosphine)palladium (0) (0.4 g) and dimethoxyethane (80 cm3) was heated under reflux for 6 h under an atmosphere of nitrogen. 20% Hydrochloric acid (200 cm3) was added and the resultant mixture extracted with diethyl ether (5×100 cm3). The combined organic layers were washed with 20% hydrochloric acid (1×100 cm3), brine (2×100 cm3) and then dried (MgSO4), filtered and evaporated down. The residue was purified by column chromatography on silica gel using a 9:1 hexane/ethyl acetate mixture as eluent and recrystallisation from ethanol to yield 4.5 g of 2-cyano-5-(4-methoxyphenyl)thiophene, K 58-60° C., I.

후처리

  1. temperatureunder reflux for 6 h under an atmosphere of nitrogen
  2. extractionthe resultant mixture extracted with diethyl ether (5×100 cm3)
  3. washThe combined organic layers were washed with 20% hydrochloric acid (1×100 cm3), brine (2×100 cm3)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated down
  7. customThe residue was purified by column chromatography on silica gel using a 9:1 hexane/ethyl acetate mixture as eluent
  8. customrecrystallisation from ethanol

출처 및 근거

ORD 기록
ord-cb6c0be3d64b43bd86806d26d6e1d8bb
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06696110B1

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