N-bromobutanimide → 5-Bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene

HRID 1880431

反応式

HRID 1880431 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([F:9])=[C:4]([CH2:10][Br:11])[CH:3]=1

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 27362985-Bromo-2-fluoro-1,3-dimethylbenzene

生成物 1

HCID 669206545-Bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene収率 100.7%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

To a stirred solution of 5-bromo-2-fluoro-1,3-dimethylbenzene (5.0 g, 25 mmol) in carbon tetrachloride (100.0 mL) was added N-bromosuccinimide (4.11 g, 23.1 mmol) and benzoyl peroxide (100.0 mg, 0.017 mmol). The reaction was heated at reflux for 7 hours. The reaction was filtered and the filtrate washed with 2N HCl, saturated aqueous sodium bicarbonate, water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was flash chromatographed (5% EtoAc/Haptanes) to obtain 6.56 g of 5-bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene as an oil product. 1H NMR (400 MHz, CDCl3) δ ppm 2.22-2.36 (s, 3 H) 4.42 (d, J=0.98 Hz, 2 H) 7.21-7.37 (m, 2 H)

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 7 hours
  3. filtrationThe reaction was filtered
  4. washthe filtrate washed with 2N HCl, saturated aqueous sodium bicarbonate, water and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (5% EtoAc/Haptanes)

出典と根拠

ORDレコード
ord-4b345bc30f60488db40c42acdba3cf03
出典データセット
uspto-grants-2012_11
特許番号
US08318762B2

関連ノート

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