Benzoyl chloride → 2-Bromobenzophenone

HRID 131059

反応式

HRID 131059 の反応式
[Li+].[Cl-].Br[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[Br:10].C([Cu])#N.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[Br:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:21]

参加物

6

反応物 4

HCID 7412Benzoyl chlorideHCID 114141,2-DibromobenzeneHCID 433294Lithium ChlorideHCID 178418546HCID 178418546、化合物

生成物 1

HCID 27355342-Bromobenzophenone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-15 °C

実験手順

A dry and argon flushed 10 mL flask, equipped with a magnetic stirrer and a septum, was charged with i-PrMgCl.LiCl (1 mL, 1.05 M in THF, 1.05 mmole), the reaction mixture was cooled to −15° C. and 1,2-dibromobenzene (235.9 mg, 1 mmole) was then added dropwise. The Br/Mg-exchange was complete after 1.5 h (checked by GC analysis of reaction aliquots, conversion more than 98%) and solution of CuCN.2LiCl (0.1 mL, 1.0 M in THF, 0.1 mmole) was added. After stirring for 10 min at −15° C. benzoyl chloride (140.6 mg, 1 mmole) was added. The reaction mixture was stirred for 1 h at −15° C. and was then quenched with sat. NH4Cl solution (2 mL) and also 5 drops of concentrated NH3 was added. The aqueous phase was extracted with ether (3×4 mL) and the organic fractions were washed with brine (5 mL), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by flash chromatography (dichloromethane) yielding the ketone (2ka) as a white cristals (219.3 mg, 84%). 1H-NMR (CDCl3, 200 MHz): δ=7.86-7.78 (m, 2H); 7.68-7.56 (m, 2H); 7.52-7.30 (m, 5H).

後処理

  1. customA dry
  2. customargon flushed 10 mL flask
  3. customequipped with a magnetic stirrer
  4. additiona septum, was charged with i-PrMgCl
  5. additionwas added
  6. customwas then quenched with sat. NH4Cl solution (2 mL) and also 5 drops of concentrated NH3
  7. additionwas added
  8. extractionThe aqueous phase was extracted with ether (3×4 mL)
  9. washthe organic fractions were washed with brine (5 mL)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo
  12. customThe crude residue was purified by flash chromatography (dichloromethane)

出典と根拠

ORDレコード
ord-6175b2d29c1a4eea9104d15720b7fd30
出典データセット
uspto-grants-2008_06
特許番号
US07384580B2

関連ノート

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