4,7-Dibromo-N-methoxy-N-methyl-2,3-dihydro-1H-indene-5-carboxamide → (4,7-Dibromo-2,3-dihydro-1H-inden-5-yl)(4-ethylphenyl)methanone

HRID 2206673Notes

Reaction equation

HRID 2206673 reaction equation
[Br:1][C:2]1[C:10]([C:11](N(OC)C)=[O:12])=[CH:9][C:8]([Br:17])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2.[CH2:18]([C:20]1[CH:25]=[CH:24][C:23]([Mg]Br)=[CH:22][CH:21]=1)[CH3:19]>C1COCC1>[Br:1][C:2]1[C:10]([C:11]([C:23]2[CH:24]=[CH:25][C:20]([CH2:18][CH3:19])=[CH:21][CH:22]=2)=[O:12])=[CH:9][C:8]([Br:17])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2

Participants

4

Reactant 2

HCID 867140174,7-Dibromo-N-methoxy-N-methyl-2,3-dihydro-1H-indene-5-carboxamideHCID 178436501HCID 178436501, compound

Product 1

HCID 71110539(4,7-Dibromo-2,3-dihydro-1H-inden-5-yl)(4-ethylphenyl)methanoneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of amide 9 (0.27 g, 0.73 mmol) in anhydrous THF (2.7 mL) was added dropwise 4-ethylphenylmagnesium bromide (3.65 mL of 0.5 M in THF, 1.83 mol) at 0° C. under nitrogen atmosphere. The mixture was warmed up to room temperature slowly and stirred at room temperature for 15 h. The reaction mixture was quenched with 1 M HCl solution (10 mL) and extracted with EtOAc (20 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the compound 10 (0.25 g, 0.62 mmol, 85%).

Workup

  1. customThe reaction mixture was quenched with 1 M HCl solution (10 mL)
  2. extractionextracted with EtOAc (20 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bd44af28324f438aa1b70c39927358cd
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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