N-bromobutanimide → 2-(Bromomethyl)-1-nitro-3-(trifluoromethyl)benzene

HRID 225991ノート

反応式

HRID 225991 の反応式
[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 81171alpha,alpha,alpha-Trifluoro-3-nitro-o-xylene

生成物 1

HCID 106781242-(Bromomethyl)-1-nitro-3-(trifluoromethyl)benzene収率 44%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

To a solution of 2-methyl-1-nitro-3-trifluoromethyl-benzene (5.0 g, 24.4 mmol) in CCl4 (300 mL) was added N-bromosuccinimide (4.35 g, 24.4 mmol) and benzoyl peroxide (0.11 g, 0.45 mmol). The mixture was heated to reflux and exposed to light (300 W) for 20 h. The mixture was cooled to room temperature, filtered and concentrated. Purification by column chromatography (EtOAc-hexanes) afforded 3.03 g (44%) of the benzyl bromide, a yellow oil. 1H NMR (400 MHz, CDCl3) δ 4.93 (s, 2 H), 7.63 (t, J=8.1 Hz, 1 H), 7.94 (d, J=7.8 Hz, 1 H), 8.06 (d, J=8.1 Hz, 1 H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (EtOAc-hexanes)

出典と根拠

ORDレコード
ord-82a5997e89054bbc8d02b3cb53adfcc0
出典データセット
uspto-grants-2009_07
特許番号
US07557135B2

反応ノート

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