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

HRID 1422144

反応式

HRID 1422144 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 183576542-(2-Fluoro-4-methylphenyl)benzaldehyde収率 71.5%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

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+ ].

後処理

  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)

出典と根拠

ORDレコード
ord-700329f16c5c438e8df54f40e3f798aa
出典データセット
uspto-grants-2000_06
特許番号
US06080773

関連ノート

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