N-bromobutanimide → 4-(Bromomethyl)-2-methoxybenzonitrile

HRID 1157862ノート

反応式

HRID 1157862 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OCC)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:11][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([O:2][CH3:1])[CH:10]=1

参加物

6

反応物 2

HCID 67184N-bromobutanimideHCID 124953732-Methoxy-4-methylbenzonitrile

生成物 1

HCID 219850074-(Bromomethyl)-2-methoxybenzonitrile収率 68.3%

試薬・触媒・溶媒 3

HCID 7187Benzoyl Peroxide触媒HCID 3283Diethyl Ether溶媒HCID 5943Carbon Tetrachloride溶媒

実験手順

To a solution of 2-methoxy-4-methylbenzonitrile (0.438 g, 2.98 mmol) in CCl4 (6 mL) was added recrystallized N-bromosuccinimide (0.544 g, 3.05 mmol) followed by benzoyl peroxide (47 mg, 0.19 mmol). The resultant mixture was heated to reflux for 45 minutes then cooled to room temperature. The mixture was diluted with diethyl ether (30 mL), filtered through filter paper, and the filtrate was concentrated. Purification of the crude material by column chromatography (6:1 hexanes-EtOAc) provided 0.46 g (68%) of 4-(bromomethyl)-2-methoxybenzonitrile as a white solid. 1H NMR (CDCl3) δ 3.96 (s, 3H), 4.45 (s, 2H), 6.99 (s, 1H), 7.03 (d, 1H, J=9 Hz), 7.53 (d, 1H, J=9 Hz).

後処理

  1. temperatureto reflux for 45 minutes
  2. filtrationfiltered
  3. filtrationthrough filter paper
  4. concentrationthe filtrate was concentrated
  5. customPurification of the crude material by column chromatography (6:1 hexanes-EtOAc)

出典と根拠

ORDレコード
ord-69f91d9a879844ba973352240240340a
出典データセット
uspto-grants-2010_10
特許番号
US07807694B2

反応ノート

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