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Dimethylformamide → 4-Bromo-2,5-difluorobenzaldehyde

HRID 572407
ノート
印刷プレビュー

反応式

HRID 572407 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([F:13])[C:10]([Br:14])=[CH:9][C:8]=1[F:15].CN([CH:19]=[O:20])C.C(OCC)(=O)C>CCOCC.C1COCC1.CCCCCC>[Br:14][C:10]1[C:11]([F:13])=[CH:12][C:7]([CH:19]=[O:20])=[C:8]([F:15])[CH:9]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 675961,4-Dibromo-2,5-difluorobenzeneHCID 178418339Butyllithium

生成物 1

HCID 224890814-Bromo-2,5-difluorobenzaldehyde収率 37%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒
HCID 8028
Tetrahydrofuran
溶媒
HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

n-Butyl lithium (3.6 ml, 7.7 mmol) was added drop wise to a solution of 1,4-dibromo-2,5-difluoro-benzene (2 g, 7.35 mmol) in dry ether at −78° C. under nitrogen atmosphere and the resulting mixture was stirred at −78° C. for 30 minutes. This was followed by the addition of DMF (0.85 ml, 11.03 mmol) in dry THF. The resultant was stirred at room temperature for 1 hour. The reaction was monitored by TLC (5% ethyl acetate in hexane). The reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride. The organic layer was concentrated and purified by column chromatography on silica gel (2% ethyl acetate in hexane) to afford 600 mg of the product (37% yield).

後処理

  1. stirringThe resultant was stirred at room temperature for 1 hour
  2. customThe reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride
  3. concentrationThe organic layer was concentrated
  4. custompurified by column chromatography on silica gel (2% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-5f194aae72294b5c9d42b853a801076a
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09029399B2

反応ノート

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