Toluene → HCID 22621153, compound

HRID 2257494Notes

Reaction equation

HRID 2257494 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([N:11]([CH3:16])[S:12]([CH3:15])(=[O:14])=[O:13])[C:3]=1[O:17][CH2:18][CH3:19].FC(F)(F)C(O)=[O:23].[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=CC=1>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[O:7])[CH2:33][C:27]([CH:32]2[CH2:31][CH2:30]2)=[O:23])=[C:4]([N:11]([CH3:16])[S:12]([CH3:15])(=[O:14])=[O:13])[C:3]=1[O:17][CH2:18][CH3:19]

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 6422Trifluoroacetic acidHCID 22620957HCID 22620957, compound

Product 1

HCID 22621153HCID 22621153, compound

Conditions

Temperature
65 °C

Procedure

A suspension of 4-bromo-3-ethoxy-2-(N-methyl-N-methylsulphonylamino)benzoyl chloride (2.45 g) in toluene (35 ml) was added to a solution of tert-butyl 3-cyclopropyl-3-oxopropionate magnesium enolate (1.3 g) in toluene (15 ml) and stirred for 2 days. Trifluoroacetic acid (1.1 ml) was added and the mixture was warmed at 65° C. for 1.5 hours, then cooled, washed with water, the organic extract dried (anhydrous magnesium sulphate) and the solvent evaporated. Purification by chromatograhpy gave 1-[4-bromo-3-ethoxy-2-(N-methyl-N-methylsulphonylamino)phenyl]-3 -cyclopropylpropane-1,3-dione (1.87 g) as a yellow semi-solid, NMR 1.05(m,2H), 1.2(m,2H), 1.5(t,3H), 1.75(m,1H), 3.0(s,3H), 3.3(s,3H), 4.2(brm,2H), 6.1(s,1H), 7.15(d,1H), 7.6(d,1H), 15.9(brs,1H).

Workup

  1. temperaturecooled
  2. washwashed with water
  3. extractionthe organic extract
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. customthe solvent evaporated
  6. customPurification by chromatograhpy

Sources & evidence

ORD record
ord-7b066198b2c346089fd2b8f37f54254a
Source dataset
uspto-grants-1997_08
Patent number
US05658858

Reaction notes

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