N-bromobutanimide → 1-(Bromomethyl)-2,5-difluoro-4-nitrobenzene

HRID 515305

반응식

HRID 515305 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[CH3:12].[Br:13]N1C(=O)CCC1=O>ClC1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH2:12][C:3]1[CH:4]=[C:5]([F:11])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimide2회HCID 2306581,4-Difluoro-2-methyl-5-nitrobenzene

생성물 1

HCID 534033971-(Bromomethyl)-2,5-difluoro-4-nitrobenzene수율 220.5%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매2회HCID 7964Chlorobenzene용매

실험 절차

1,4-Difluoro-2-methyl-5-nitrobenzene (1 g) was dissolved in chlorobenzene (6 mL) and N-bromosuccinimide (1.54 g) added followed by benzoyl peroxide (0.2 g). The reaction mixture was stirred at reflux for 2.5 hours then additional benzoyl peroxide (0.2 g) and N-bromosuccinimide (1.54 g) were added. The reaction was refluxed for 2 hours then was cooled to room temperature, quenched with water and extracted with dichloromethane (3×). The combined organics were dried and concentrated under reduced pressure. The oil obtained was triturated with diethyl ether, filtered and the filtrate concentrated under reduced pressure to yield the title compound (3.21 g).

후처리

  1. temperatureat reflux for 2.5 hours
  2. temperatureThe reaction was refluxed for 2 hours
  3. customquenched with water
  4. extractionextracted with dichloromethane (3×)
  5. customThe combined organics were dried
  6. concentrationconcentrated under reduced pressure
  7. customThe oil obtained
  8. customwas triturated with diethyl ether
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-502793d67fcb49f4b86ae129b0caa852
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108939B2

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