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

HRID 73127

반응식

HRID 73127 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-8541a7b1c057457fbe210b8acc3919ea
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829033B2

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