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

HRID 1360678ノート

反応式

HRID 1360678 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 162272363-(Bromomethyl)-4-fluorobenzonitrile収率 74.5%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e08561509d4340ada56c3f86cd87b461
出典データセット
uspto-grants-2011_02
特許番号
US07879875B2

反応ノート

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