Hydrogen Bromide → 5-Bromo-2-methylbenzonitrile

HRID 657327노트

반응식

HRID 657327 반응식
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]

참가 물질

5

반응물 3

HCID 260Hydrogen Bromide2회HCID 27353655-Amino-2-methylbenzonitrileHCID 23668193Sodium Nitrite

생성물 1

HCID 129940045-Bromo-2-methylbenzonitrile수율 77%

시약·촉매·용매 1

HCID 962Water용매4회

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-721830c618f34be2bb58f9864f44935f
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071588B2

반응 노트

불러오는 중…