1-Naphthoic acid → 2-(4-Fluorophenoxy)-4-tert-butylbenzoic acid

HRID 79092

반응식

HRID 79092 반응식
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7](Br)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C(O)=O)C2C(=CC=CC=2)C=CC=1>C1(C)C=CC=CC=1.C1C=CC=CC=1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+].[Cu+].CCOC(C)=O>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])=[CH:18][CH:17]=1

참가 물질

8

반응물 4

HCID 68471-Naphthoic acidHCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 2363522-Bromo-4-tert-butylbenzoic acid

생성물 1

HCID 589880892-(4-Fluorophenoxy)-4-tert-butylbenzoic acid수율 39%

시약·촉매·용매 3

HCID 2734754Benzene;bis(copper(1+));bis(trifluoromethanesulfonate)촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A stirred suspension of 4-tert-butyl-2-bromobenzoic acid (0.26 g, 1.0 mmol), 4-fluoro phenol (0.22 g, 2.0 mmol), cesium carbonate (0.65 g, 2.0 mmol), copper trifluoromethanesulfonate-benzene complex (13 mg, 25 μmol), 1-naphthoic acid (0.34 g, 2.0 mmol), and 4 Å molecular sieves (0.25 g) in toluene (10 mL) and EtOAc (5 μL) was heated at 110° C. for 16 h. The reaction was concentrated under reduced pressure and purified by silica gel chromatography (0%-5% MeOH—CH2Cl2) to afford 2-(4-fluorophenoxy)-4-tert-butylbenzoic acid (0.11 g, 39% yield) as a white solid. LC/MS: m/z 289.0 (M+H)+ at 3.58 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, CDCl3) δ 8.12 (d, J=8.3 Hz, 1H), 7.24 (d, J=1.7 Hz, 1H), 7.14-7.05 (m, 4H), 6.84 (d, J=1.6 Hz, 1H), 1.23 (s, 9H) ppm.

후처리

  1. concentrationThe reaction was concentrated under reduced pressure
  2. custompurified by silica gel chromatography (0%-5% MeOH—CH2Cl2)

출처 및 근거

ORD 기록
ord-ae47c4adfc9d403c835af054aab39927
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841483B2

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