Water → 2-(4-Bromopyridin-2-yl)-1-(4-chlorophenyl)ethanone

HRID 1918194

反応式

HRID 1918194 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].O>O1CCCC1>[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

6

反応物 4

HCID 962WaterHCID 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 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

1.0 g (5.8 mmol) of 4-bromo-2-methylpyridine and 2.14 g (11.6 mmol) of ethyl 4-chlorobenzoate are placed under a stream of argon in a round-bottomed flask and dissolved in 10 ml of anhydrous tetrahydrofuran. The solution is cooled to 0° C. and 12 ml of a lithium hexamethyldisilazane (LiHMDS) solution (1M in tetrahydrofuran) are added. After addition, the mixture is heated at 45° C. for 3 h and cooled to ambient temperature, and then water is added. The tetrahydrofuran is subsequently evaporated under reduced pressure and the aqueous phase is extracted three times with ether. The organic phase is separated, dried and concentrated under reduced pressure. The residue obtained is purified by chromatography on silica gel, elution being carried out with a mixture of dichloromethane and heptane. 1.11 g (62%) of compound are obtained.

後処理

  1. additionAfter addition
  2. temperaturethe mixture is heated at 45° C. for 3 h
  3. temperaturecooled to ambient temperature
  4. customThe tetrahydrofuran is subsequently evaporated under reduced pressure
  5. extractionthe aqueous phase is extracted three times with ether
  6. customThe organic phase is separated
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue obtained
  10. customis purified by chromatography on silica gel, elution
  11. additionbeing carried out with a mixture of dichloromethane and heptane

出典と根拠

ORDレコード
ord-f76a6fc69c094e18a7c0caee1e8a33be
出典データセット
uspto-grants-2013_12
特許番号
US08618301B2

関連ノート

読み込み中…