Benzoyl Peroxide → 3-(Bromomethyl)-4-fluorobenzonitrile

HRID 1360678노트

반응식

HRID 1360678 반응식
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[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][CH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[F:1])[C:6]#[N:7]

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27791804-Fluoro-3-methylbenzonitrile

생성물 1

HCID 162272363-(Bromomethyl)-4-fluorobenzonitrile수율 74.5%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a solution of 4-fluoro-3-methylbenzonitrile (15.0 g, 111 mmol), in CCl4 (600 mL) was added N-bromosuccinimide (23.7 g, 133 mmol), and benzoyl peroxide (5.38 g, 22.2 mol). The mixture was irradiated with a sunlamp (250 W) to create a gentle reflux. After 0.5 hours of exposure the reaction was complete by TLC. The reaction mixture was cooled and filtered through celite. The filtrate was condensed in vacou to yield brown oil. The crude residue was purified via silica gel column chromatography (hexanes/ethyl acetate) to yield 17.7 g of the desired product.

후처리

  1. customThe mixture was irradiated with a sunlamp (250 W)
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through celite
  4. customcondensed in vacou
  5. customto yield brown oil
  6. customThe crude residue was purified via silica gel column chromatography (hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-e08561509d4340ada56c3f86cd87b461
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879875B2

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