Dimethylformamide → HCID 22996227、化合物

HRID 1167296ノート

反応式

HRID 1167296 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH3:13].[CH3:14][N:15](C)C=O>C(OCC)C.C(=O)(O)[O-].[Na+].[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]#[N:15])=[C:3]([O:10][CH2:11][CH2:12][CH3:13])[CH:4]=1

参加物

7

反応物 2

HCID 6228DimethylformamideHCID 229962121-Bromo-4-methoxy-2-propoxy-benzene

生成物 1

HCID 22996227HCID 22996227、化合物収率 74%

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒HCID 3283Diethyl Ether溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
95 °C

実験手順

To a solution of 1-bromo-4-methoxy-2-propoxy-benzene (500 mg, 2.04 mmol) in dimethylformamide (10 mL) at room temperature was added zinc cyanide (240 mg, 2.04 mmol). The reaction mixture was degassed by passing argon through for 2 h before tetrakis(triphenylphosphine)palladium (236 mg, 0.204 mmol) was added. The reaction mixture was heated at 90-100° C. under argon for 12 h. The reaction mixture was taken up in diethyl ether (10 mL) and sodium bicarbonate solution (2 mL). The product was extracted with diethyl ether (2×20 mL). The organic layers were washed with water (1×5 mL), brine (1×5 mL), and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 15-20% ethyl acetate in hexanes yielded 4-methoxy-2-propoxy-benzonitrile (290 mg, 74%) as white solids.

後処理

  1. customThe reaction mixture was degassed
  2. customthrough for 2 h
  3. additionwas added
  4. extractionThe product was extracted with diethyl ether (2×20 mL)
  5. washThe organic layers were washed with water (1×5 mL), brine (1×5 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe solid was then filtered off
  8. concentrationthe filtrate was concentrated in vacuo
  9. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  10. washeluting with 15-20% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-edad628ce2f84917a9920d775e20f723
出典データセット
uspto-grants-2003_09
特許番号
US06617346B1

反応ノート

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