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

HRID 1157862노트

반응식

HRID 1157862 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

HCID 219850074-(Bromomethyl)-2-methoxybenzonitrile수율 68.3%

시약·촉매·용매 3

HCID 7187Benzoyl Peroxide촉매HCID 3283Diethyl Ether용매HCID 5943Carbon Tetrachloride용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-69f91d9a879844ba973352240240340a
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807694B2

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