Dimethylformamide → 6-Bromo-2-fluoro-3-propylbenzaldehyde

HRID 718482ノート

反応式

HRID 718482 の反応式
[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[C:12]([F:19])[CH:11]=1.CN([CH:23]=[O:24])C>C1COCC1>[Br:9][C:10]1[C:11]([CH:23]=[O:24])=[C:12]([F:19])[C:13]([CH2:16][CH2:17][CH3:18])=[CH:14][CH:15]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 215898314-Bromo-2-fluoro-1-propylbenzene

生成物 1

HCID 866960636-Bromo-2-fluoro-3-propylbenzaldehyde収率 39.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

Under a nitrogen atmosphere, LDA (50.7 mL, 56.25 mmol) was slowly added dropwise, at −70° C. or lower, to a THF (100 mL) solution of 4-bromo-2-fluoro-1-propylbenzene (50) (11.1 g, 51.13 mmol). The reaction mixture was agitated at −70° C. or lower for 1 hour, and then DMF (6.15 g, 76.70 mmol) was slowly added dropwise thereto. The reaction mixture was returned to room temperature, and then quenched with 100 mL of 1N hydrochloric acid aqueous solution, and extracted with 60 mL of toluene 3 times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, dried over magnesium sulfate and a solvent was distilled off by evaporator. The residue was purified by silica gel column chromatography, and thus 6-bromo-2-fluoro-3-propylbenzaldehyde (51) (5.0 g, yield 36%) was obtained.

後処理

  1. customwas returned to room temperature
  2. customquenched with 100 mL of 1N hydrochloric acid aqueous solution
  3. extractionextracted with 60 mL of toluene 3 times
  4. washCombined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationa solvent was distilled off by evaporator
  7. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-0f1cdce2f3b84a528713ea345a888ec4
出典データセット
uspto-grants-2015_11
特許番号
US09193908B2

反応ノート

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