Hydrogen Bromide → 5-Bromo-2-methylbenzonitrile

HRID 657327ノート

反応式

HRID 657327 の反応式
N[C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8].N([O-])=O.[Na+].[BrH:15]>O>[Br:15][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8]

参加物

5

反応物 3

HCID 260Hydrogen Bromide2 回HCID 27353655-Amino-2-methylbenzonitrileHCID 23668193Sodium Nitrite

生成物 1

HCID 129940045-Bromo-2-methylbenzonitrile収率 77%

試薬・触媒・溶媒 1

HCID 962Water溶媒4 回

反応条件

温度
50 °C

実験手順

Water (13.5 mL), HBr (74%, 14.4 mL) and 5-amino-2-methylbenzonitrile (2.0 g, 15.1 mmol) dissolved in water (24 mL) was added to a flask and heated to 50° C. for 20 min. Then the mixture was cooled to 0˜5° C., and a solution of NaNO2 (1.2 g, 17.4 mmol) in water was added. The reaction mixture was stirred for 10 min at 0˜5° C., then was warmed to 40° C. A solution of CuBr (6.5 g, 45.1 mmol) in water (36 mL) and HBr (7.2 mL) was added to the mixture, and refluxed for 2 h. The mixture was extracted with AcOEt, and the organic layer was washed by saturated NaHCO3 solution and brine, and dried over Na2SO4. The crude product was purified by flask chomatograph (PE:EA=50:1), obtaining 2.3 g of 5-bromo-2-methylbenzonitrile as a white solid (yield: 77%). 1H NMR (400 MHz, CDCl3) δ 7.72 (s, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H), 2.51 (s, 3H).

後処理

  1. additionwas added to a flask
  2. temperatureThen the mixture was cooled to 0˜5° C.
  3. temperaturewas warmed to 40° C
  4. temperaturerefluxed for 2 h
  5. extractionThe mixture was extracted with AcOEt
  6. washthe organic layer was washed by saturated NaHCO3 solution and brine
  7. dry with materialdried over Na2SO4
  8. customThe crude product was purified by flask chomatograph (PE:EA=50:1)

出典と根拠

ORDレコード
ord-721830c618f34be2bb58f9864f44935f
出典データセット
uspto-grants-2011_12
特許番号
US08071588B2

反応ノート

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