Ethyl 4-chlorobenzoate → 2-(4-Bromopyridin-2-yl)-1-(4-chlorophenyl)ethanone

HRID 1190855

反応式

HRID 1190855 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[Cl:9][C:10]1[CH:20]=[CH:19][C:13]([C:14](OCC)=[O:15])=[CH:12][CH:11]=1.C[Si](C)(C)N[Si](C)(C)C.[Li]>O1CCCC1.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:14]([C:13]2[CH:19]=[CH:20][C:10]([Cl:9])=[CH:11][CH:12]=2)=[O:15])[CH:3]=1

参加物

7

反応物 3

HCID 81785Ethyl 4-chlorobenzoateHCID 27628354-Bromo-2-methylpyridineHCID 57426343Lithium bis(trimethylsilyl)amide

生成物 1

HCID 672466412-(4-Bromopyridin-2-yl)-1-(4-chlorophenyl)ethanone収率 93%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

Under a stream of nitrogen, 5 g (29.07 mmol) of 4-bromo-2-methylpyridine and 11.27 g (61.04 mmol) of ethyl 4-chlorobenzoate are placed in a round-bottomed flask and dissolved in 50 mL of anhydrous tetrahydrofuran. The solution is cooled to 5° C. and 70 mL (70 mmol) of a lithium hexamethyldisilazane solution (1M in tetrahydrofuran) are added dropwise. After addition, the mixture is stirred at room temperature for 2 hours, cooled to 5° C., and 100 mL of water are then gradually added. The medium is then diluted with 250 mL of ethyl acetate and 100 mL of water. The organic phase is separated out and the aqueous phase is extracted twice with 100 mL of ethyl acetate. The organic phases are then combined, dried over sodium sulfate and filtered. 15 g of silica are then added to the filtrate, which is then concentrated under reduced pressure. The powder obtained is used as solid deposit for a chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (9/1). 8.4 g (93%) of compound are obtained in the faun of a yellow powder.

後処理

  1. additionAfter addition
  2. temperaturecooled to 5° C.
  3. customThe organic phase is separated out
  4. extractionthe aqueous phase is extracted twice with 100 mL of ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. addition15 g of silica are then added to the filtrate, which
  8. concentrationis then concentrated under reduced pressure
  9. customThe powder obtained
  10. washeluting with a mixture of cyclohexane and ethyl acetate (9/1)

出典と根拠

ORDレコード
ord-40d0f7c59b3d436b984409578b2de185
出典データセット
uspto-grants-2014_03
特許番号
US08680096B2

関連ノート

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