Potassium Carbonate → 4-[(3-Fluorophenyl)methoxy]benzonitrile

HRID 73127

反応式

HRID 73127 の反応式
OC1O[C@H](C)[C@H](O)C[C@H]1O.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)#[N:12].C([O-])([O-])=O.[K+].[K+].[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Br>CC(C)=O>[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]#[N:12])=[CH:14][CH:15]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 680073-Fluorobenzyl bromideHCID 160540D-Abequose

生成物 1

HCID 22293834-[(3-Fluorophenyl)methoxy]benzonitrile収率 87.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

(Nakamoto, Kazutaka; Tsukada, Itaru; Tanaka, Keigo; Matsukura, Masayuki; Haneda, Toru; Inoue, Satoshi; Ueda, Norihiro; Abe, Shinya; Hata, Katsura; Watanabe, Naoaki, WO 2005033079 (2005)). A mixture of 4-cyanophenol (11.91 g, 100.0 mmol), K2CO3 (55.20 g, 400.0 mmol), and 3-fluorobenzylbromide (22.68 g, 120.0 mmol) were heated in acetone (400 mL) at reflux (5 h). The volatiles were evaporated and the residue was diluted in CH2Cl2 (300 mL), and then washed with H2O (500 mL), dried (MgSO4), and concentrated in vacuo to give white needles (19.81 g, 87%): Rf=0.45 (hexanes/EtOAc 9/1); mp 104-105° C.; 1H NMR (CDCl3) δ 5.11 (s, CH2O), 6.98-7.20 (m, 5 ArH), 7.33-7.41 (m, 1 ArH), 7.59 (d, J=8.7 Hz, 2 ArH); HRMS (M+Na+) (ESI+) 250.0641 [M+Na+] (calcd for C14H10NONa+250.0641).

後処理

  1. temperatureat reflux (5 h)
  2. customThe volatiles were evaporated
  3. additionthe residue was diluted in CH2Cl2 (300 mL)
  4. washwashed with H2O (500 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8541a7b1c057457fbe210b8acc3919ea
出典データセット
uspto-grants-2014_09
特許番号
US08829033B2

関連ノート

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