Benzoyl Peroxide → 2-(Bromomethyl)-4-fluorobenzonitrile

HRID 505695

반응식

HRID 505695 반응식
[CH3:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 38260554-Fluoro-2-methylbenzonitrile

생성물 1

HCID 219849902-(Bromomethyl)-4-fluorobenzonitrile수율 25%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

A solution of 2-methyl-4-fluoro-benzonitrile (3.5 g, 25.9 mmol) in 40 mL of carbon tetrachloride was treated with N-Bromosuccinimide (4.6 g, 25.9 mmol) and benzoylperoxide (157 mg, 0.65 mmol). The mixture was heated to reflux for 3 hours, cooled to room temperature and allowed to stir overnight. The solids were filtered off and washed with carbon tetrachloride. The filtrate was condensed and purified by normal phase flash column chromatography on a 50 g silica gel column (5-50% ethyl acetate/hexanes gradient). Two peaks separated. It was determined that the second eluting peak is the desired product. Pure fractions of this peak were pooled and concentrated in vacuo to yield 2-(bromomethyl)-4-fluorobenzonitrile (1.35 g, 0.63 mmol, 25% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.79 (s, 2H), 7.44 (dt, J=8.59, 2.69 Hz, 1H), 7.68 (dd, J=9.53, 2.55 Hz, 1H), 8.01 (dd, J=8.59, 5.64 Hz, 1H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe solids were filtered off
  4. washwashed with carbon tetrachloride
  5. customcondensed
  6. custompurified by normal phase flash column chromatography on a 50 g silica gel column (5-50% ethyl acetate/hexanes gradient)
  7. customTwo peaks separated
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-15e7e22a8e164223882fa189072229dc
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781428B2

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