Iodoethane → 1-Ethoxy-5-fluoro-4-methyl-2-nitrobenzene

HRID 419621

反応式

HRID 419621 の反応式
[CH3:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.I[CH2:14][CH3:15].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:9][CH2:14][CH3:15])=[CH:6][C:7]=1[F:8]

参加物

6

反応物 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 127824115-Fluoro-4-methyl-2-nitrophenol

生成物 1

HCID 594528831-Ethoxy-5-fluoro-4-methyl-2-nitrobenzene収率 60.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

実験手順

4-Methyl-5-fluoro-2-nitrophenol (11.1 g, 65.0 mmol) and iodoethane (12.2 g, 78.0 mmol) were dissolved in 100 mL of DMSO with stirring. K2CO3 (13.5 g, 97.5 mmol) was added. The reaction was stirred for 3 h and then diluted with DCM and filtered. The filtrate was poured into H2O and extracted with DCM. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound of step A (8.0 g, 39.4 mmol) as a pale yellow crystalline solid. 1H NMR (400 MHz, CDCl3) δ 7.76 (d, J=8.1 Hz, 1H), 6.70 (d, J=11.0 Hz, 1H), 4.10 (q, J=7.0 Hz, 2H), 2.22 (s, 3H), 1.45 (t, J=7.0 Hz, 3H).

後処理

  1. stirringThe reaction was stirred for 3 h
  2. filtrationfiltered
  3. additionThe filtrate was poured into H2O
  4. extractionextracted with DCM
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f8596cf6d2564e7abe2e4f04878f3b32
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

関連ノート

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