Azobisisobutyronitrile → 2-Bromomethyl-3-fluoro-6-nitro-benzoic acid methyl ester

HRID 604263노트

반응식

HRID 604263 반응식
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([F:13])[C:5]=1[CH3:14].[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([F:13])[C:5]=1[CH2:14][Br:16]

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 59849164Methyl 3-fluoro-2-methyl-6-nitrobenzoate

생성물 1

HCID 598492172-Bromomethyl-3-fluoro-6-nitro-benzoic acid methyl ester수율 54%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

반응 조건

온도
85 °C

실험 절차

To a suspension of 3-fluoro-2-methyl-6-nitro-benzoic acid methyl ester (6.1 g, 28.6 mmol) and N-bromosuccinimide in 70 mL of CCl4 is added 2,2′-azobisisobutyronitrile at room temperature under nitrogen atmosphere. The reaction mixture is stirred at 85° C. for 6 hours under N2, then cooled to room temperature and filtrated. The filtrate is extracted with CH2Cl2 and washed with aqueous NaHCO3 solution followed by brine, dried over Na2SO4, filtered and evaporated in vacuo. The residue is purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to afford the 2-bromomethyl-3-fluoro-6-nitro-benzoic acid methyl ester (4.48 g, 15.3 mmol, 54%) as yellow oil. 1H-NMR (400 MHz, δ, ppm) CDCl3: 4.01 (s, 3H), 4.53 (d, 2H), 7.31 (dd, 1H), 8.17 (dd, 1H).

후처리

  1. temperaturecooled to room temperature
  2. filtrationfiltrated
  3. extractionThe filtrate is extracted with CH2Cl2
  4. washwashed with aqueous NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue is purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-80d4feb0551e4a54aecb612d0f5cd661
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910585B2

반응 노트

불러오는 중…