Methanol → 4-Bromo-2-methoxybenzonitrile

HRID 29231

反応式

HRID 29231 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 223467024-Bromo-2-methoxybenzonitrile収率 95.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dfe0619ae872459c9e0030ceb8e4fcb6
出典データセット
uspto-grants-2008_09
特許番号
US07420066B2

関連ノート

読み込み中…