Water → HCID 63319772, compound

HRID 2251563Notes

Reaction equation

HRID 2251563 reaction equation
[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1.[CH:19]1([C:22](N2C3C=CC=CC=3N=N2)=[O:23])[CH2:21][CH2:20]1.O>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH2:17][C:22]([CH:19]2[CH2:21][CH2:20]2)=[O:23])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7466p-BromoacetophenoneHCID 903307Benzotriazol-1-yl(cyclopropyl)methanoneHCID 2724682Lithium diisopropylamide

Product 1

HCID 63319772HCID 63319772, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a −78C solution of LDA (generated from 8 ml of 2.5 M nBuLi and 2.1 ml of diisopropylamine) in THF (120 ml) was added dropwise, over 80 min, a solution a 4′-bromoacetophenone (2.98 g, 14.97 mmol) in THF (45 ml). The mixture continued to stir at −78C for 1 h, followed by addition of 1-(cyclopropylcarbonyl)-1H-1,2,3-benzotriazole (2.56 g, 13.65 mmol) in THF (45 ml). The mixture was warmed to rt overnight. The yellow mixture was poured into water and extracted with Et2O (2×300 ml). The combined organic phases were washed with water, dried with MgSO4, and concentrated in vacuo. The crude material was purified by flash chromatography (CH2Cl2/hexanes, 10:90 to 30:70) to yield 1-(4-bromophenyl)-3-cyclopropyl-1,3-propanedione as an orange solid (1.60 g, 44%).

Workup

  1. extractionextracted with Et2O (2×300 ml)
  2. washThe combined organic phases were washed with water
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (CH2Cl2/hexanes, 10:90 to 30:70)

Sources & evidence

ORD record
ord-0184ca8503184c1480fc343dfc366aca
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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