Ethyl Bromide → 1-Ethoxy-2,5-difluoro-4-nitrobenzene

HRID 1811549ノート

反応式

HRID 1811549 の反応式
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH3:21].ICC>C(#N)C>[CH2:20]([O:12][C:3]1[CH:4]=[C:5]([F:11])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1])[CH3:21]

参加物

6

反応物 4

HCID 6332Ethyl BromideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27824902,5-Difluoro-4-nitrophenol

生成物 1

HCID 685658171-Ethoxy-2,5-difluoro-4-nitrobenzene収率 88.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

To a solution of 2,5-difluoro-4-nitro-phenol (4.86 g, 28.2 mmol) in acetonitrile (50 mL), potassium carbonate (4.7 g, 34 mmol) and bromoethane (4.21 mL, 56.4 mmol) were added. After stirring at 70° C. for 3.5 hours, iodoethane (2.73, 33.8 mmol) was added and mixture was stirred at 80° C. After 20 hours, mixture was concentrated and extracted with methylene chloride and 2M NaOH solution. Organic phases were dried over magnesium sulfate, filtered, and concentrated to give 1-ethoxy-2,5-difluoro-4-nitro-benzene as a yellow solid (5.05 g, 88%). 1HNMR (CDCl3, 400 MHz) δ 7.92-7.88 (m, 1H), 6.82-6.78 (m, 1H), 4.21-4.16 (q, 1H), 4.13-4.07 (q, J=7.0 Hz, 2H), 1.54-1.51 (t, J=7.0 Hz, 3H).

後処理

  1. stirringmixture was stirred at 80° C
  2. waitAfter 20 hours
  3. concentrationmixture was concentrated
  4. extractionextracted with methylene chloride and 2M NaOH solution
  5. dry with materialOrganic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-286ff2a7d1a84cddbf78d767383003a3
出典データセット
uspto-grants-2013_01
特許番号
US08362248B2

反応ノート

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