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

HRID 1811549노트

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HRID 1811549 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 685658171-Ethoxy-2,5-difluoro-4-nitrobenzene수율 88.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-286ff2a7d1a84cddbf78d767383003a3
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362248B2

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