Sodium Carbonate → 2-(2-Fluoro-4-methylphenyl)benzaldehyde

HRID 1422144

반응식

HRID 1422144 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O)=[O:11].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C(CCO)=CC=CC=1>C(Cl)Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:10]=[O:11]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 882672-Methylphenethyl alcoholHCID 2921892-Formylphenylboronic acidHCID 5732804-Bromo-3-fluorotoluene

생성물 1

HCID 183576542-(2-Fluoro-4-methylphenyl)benzaldehyde수율 71.5%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2 g of 4-bromo-3-fluorotoluene, 1.75 g of 2-formylbenzeneboronic acid, 0.36 g of tetrakis(triphenylphosphine)-palladium (0) and 11.6 ml of 2N aqueous sodium carbonate, in 50 ml of a 9:1 mixture of toluene-ethanol was heated to 100° C. for 3 h. The mixture was cooled to room temperature, diluted with 100 ml of methylene chloride and washed with 50 ml of 5% sodium bicarbonate containing 5 ml of 0.880 ammonia. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure. The resulting oil was purified by chromatography on silica gel eluting with ethyl acetate-heptane (1:3) to give 1.62 g of 2-(2-fluoro-4-methylphenyl)benzaldehyde as an oil, GC-M.S. (E.I.) (M/Z): 214 [M+ ].

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with 50 ml of 5% sodium bicarbonate containing 5 ml of 0.880 ammonia
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customThe resulting oil was purified by chromatography on silica gel eluting with ethyl acetate-heptane (1:3)

출처 및 근거

ORD 기록
ord-700329f16c5c438e8df54f40e3f798aa
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06080773

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