Toluene → HCID 22621153, compound

HRID 841163Notes

Reaction equation

HRID 841163 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 chromatography 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(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 chromatography

Sources & evidence

ORD record
ord-51e5d59a742e46dcb4f714d1a4aa5279
Source dataset
uspto-grants-2002_04
Patent number
US06369270B1

Reaction notes

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