2,6-Dimethylphenol → 2,6-Dimethylphenyl pentafluorobenzyl ether

HRID 440160

반응식

HRID 440160 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[F:10][C:11]1[C:16]([CH2:17]Br)=[C:15]([F:19])[C:14]([F:20])=[C:13]([F:21])[C:12]=1[F:22].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[F:10][C:11]1[C:16]([CH2:17][O:9][C:3]2[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[C:15]([F:19])[C:14]([F:20])=[C:13]([F:21])[C:12]=1[F:22]

참가 물질

6

반응물 4

HCID 113352,6-DimethylphenolHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 74484Pentafluorobenzyl bromide

생성물 1

HCID 110557542,6-Dimethylphenyl pentafluorobenzyl ether수율 96%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of 2,6-dimethylphenol (5 mmol), pentafluorobenzyl bromide (1.3 g, 5 mmol), potassium carbonate (5 g), acetone (30 ml), and 18-crown-6 ether (0.1 g) were stirred under reflux for 5 hours. Work-up procedure was the same as above. Yield: 96%; m.p.: 81°-82° C.; 1H NMR, δ: 2.37 (s, 6H, CH3), 4.91 (s, 2H, CH2O), 6.96-7.16 (m, 3H, H-Ar) ppm; 13C NMR, δ: 15.7 (CH3), 59.9 (CH2O), 110.7 (C1', 2JC-F =18 Hz), 124.6 (C4), 129.0 (C3 & C5), 131.1 (C2 & C6), 137.6 (C2' & C6', JC-F =253 Hz), 141.7 (C4', JC-F =255 Hz), 145.9 (C3' & C5', JC-F =250 Hz ), 154.6 (C1) ppm.

후처리

  1. temperatureunder reflux for 5 hours

출처 및 근거

ORD 기록
ord-ba7575b8e544453dbc53edf8ee64ce8c
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05516931

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