Sulfuric Acid → N-[(3-Bromophenyl)(phenyl)methylene]-2,6-diisopropylaniline

反応式

[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)[CH:5]=[CH:6][CH:7]=1.[Si](OCC)(OCC)(OCC)OCC.[CH:29]([C:32]1[CH:38]=[CH:37][CH:36]=[C:35]([CH:39]([CH3:41])[CH3:40])[C:33]=1[NH2:34])([CH3:31])[CH3:30].OS(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:34][C:33]2[C:35]([CH:39]([CH3:40])[CH3:41])=[CH:36][CH:37]=[CH:38][C:32]=2[CH:29]([CH3:31])[CH3:30])[CH:5]=[CH:6][CH:7]=1

参加物

反応物 4

HCID 1118Sulfuric Acid

HCID 6517Tetraethoxysilane

HCID 32484Diisopropylaniline

HCID 705483-Bromobenzophenone

生成物 1

HCID 58238566N-[(3-Bromophenyl)(phenyl)methylene]-2,6-diisopropylaniline収率 84%

反応条件

温度: 170 °C

実験手順

In 25 mL Claisens flask in an argon atmosphere, a mixture of 5.22 g (20.0 mmol) of 16, 5.00 g (24.0 mmol) of Si(OEt)4, and 3.90 g (22.0 mmol) of 2,6-diisopropylaniline was heated to 170° C., and then 0.13 mL of 96% H2SO4 was added. This mixture was stirred at this temperature for 50 hr, and the formed ethanol was slowly distilled off. Later, 300 mL of cold water was added, and the product was extracted with 2×70 mL of diethyl ether. The combined extract was dried over K2CO3 and then evaporated to dryness. The product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether, 100:1, vol.). This procedure gave 7.06 g (84%) of the title product 17.