Dimethylformamide → 5-(1-Fluorocyclopropyl)-2-methoxybenzaldehyde

HRID 406398ノート

反応式

HRID 406398 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([C:13]2([F:16])[CH2:15][CH2:14]2)[CH:10]=[CH:9][C:8]=1[O:17][CH3:18].CN([CH:22]=[O:23])C.C(=O)(O)[O-].[Na+]>C1COCC1>[F:16][C:13]1([C:11]2[CH:10]=[CH:9][C:8]([O:17][CH3:18])=[C:7]([CH:12]=2)[CH:22]=[O:23])[CH2:15][CH2:14]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 666334672-Bromo-4-(1-fluorocyclopropyl)-1-methoxybenzeneHCID 178418339Butyllithium

生成物 1

HCID 866626555-(1-Fluorocyclopropyl)-2-methoxybenzaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

n-Butyllithium (2.7M solution in hexane, 3.42 ml) was added at −78° C. to a solution of 2-bromo-4-(1-fluorocyclopropyl)-1-methoxybenzene (1.88 g) in THF (62 ml), followed by addition of a solution of DMF (650 μl) in THF. After the reaction mixture was stirred at −78° C. for 30 minutes, a saturated aqueous solution of sodium bicarbonate was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (1.00 g).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-4375d25adb354f42be72c9add84c9f60
出典データセット
uspto-grants-2014_06
特許番号
US08754100B2

反応ノート

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