Methanol → 4-Bromo-2-methoxybenzonitrile

HRID 29231

반응식

HRID 29231 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.CO.[C:13](=O)([O-])[O-:14].[K+].[K+].C(Cl)Cl>CN(C=O)C.O.CCOCC>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:14][CH3:13])[CH:3]=1

참가 물질

8

반응물 4

HCID 887MethanolHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 7360294-Bromo-2-fluorobenzonitrile

생성물 1

HCID 223467024-Bromo-2-methoxybenzonitrile수율 95.6%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

A mixture of 4-bromo-2-fluoro-benzonitrile (15.0 g, 75.0 mmol), methanol (30.4 mL, 350 mmol) and potassium carbonate (31.1 g, 225 mmol) in DMF (150 mL) was stirred under argon at 55° C. overnight. At this point TLC (100% methylene chloride) revealed no starting material, and the reaction mixture was poured into ether (300 mL) and water (150 mL). The layers were separated, and the organic layer was washed with water (150 mL) and brine (50 mL), dried over Mg2SO4, filtrated, and concentrated under reduced pressure, providing (15.2 g, 95.5%) of 4-bromo-2-methoxy-benzonitrile as a white solid. 1H-NMR (CDCl3) δ 7.41 (d, J=8.1 Hz, 1H), 7.16 (dd, J=8.1, 1.6 Hz, 1H), 7.13 (d, J=1.6 Hz, 1H), 3.93 (s, 3H); MS GC-MS (M+=211; RT=6.15 min).

후처리

  1. customThe layers were separated
  2. washthe organic layer was washed with water (150 mL) and brine (50 mL)
  3. dry with materialdried over Mg2SO4
  4. filtrationfiltrated
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-dfe0619ae872459c9e0030ceb8e4fcb6
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420066B2

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