Sulfuric Acid → HCID 178422466, compound

HRID 1042527

Reaction equation

HRID 1042527 reaction equation
[Br:1][C:2]1[C:3]([OH:17])=[C:4]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Si](OCC)(OCC)(OCC)OCC.[CH:31]([C:34]1[CH:40]=[CH:39][CH:38]=[C:37]([CH:41]([CH3:43])[CH3:42])[C:35]=1[NH2:36])([CH3:33])[CH3:32].OS(O)(=O)=O>>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4](/[C:9](=[N:36]/[C:35]2[C:37]([CH:41]([CH3:42])[CH3:43])=[CH:38][CH:39]=[CH:40][C:34]=2[CH:31]([CH3:33])[CH3:32])/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[OH:17]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6517TetraethoxysilaneHCID 32484DiisopropylanilineHCID 12925474(3-Bromo-2-hydroxy-5-methylphenyl)(phenyl)methanone

Product 1

HCID 178422466HCID 178422466, compoundYield 69.1%

Conditions

Temperature
170 °C

Procedure

In 50 mL Claisen's flask in argon atmosphere, a mixture of 13.5 g (46.3 mmol) of 26, 20.2 g (97.2 mmol) of Si(OEt)4, and 9.03 g (50.9 mmol) of 2,6-diisopropylaniline was heated to 170° C., and then 0.37 mL of 96% H2SO4 was added. This mixture was stirred at this temperature for 35 hr, and the formed ethanol was slowly distilled off. Later, 300 mL of cold water was added, and the product was extracted with 2×100 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 14.4 g (69%) of the title product.

Workup

  1. distillationthe formed ethanol was slowly distilled off
  2. additionLater, 300 mL of cold water was added
  3. extractionthe product was extracted with 2×100 mL of diethyl ether
  4. extractionThe combined extract
  5. dry with materialwas dried over K2CO3
  6. customevaporated to dryness
  7. customThe product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether, 100:1, vol.)

Sources & evidence

ORD record
ord-81172488656d4ea890cc22abb85e795d
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Linked notes

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