5-Fluoro-1-indanone → HCID 45090442, compound

HRID 1181427Notes

Reaction equation

HRID 1181427 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.[CH3:12][Mg]Br>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([CH3:12])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 1365375-Fluoro-1-indanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 45090442HCID 45090442, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-fluoro-1-indanone (25 g, 0.17 mol) in dry THF (100 ml) was added dropwise to a solution of methyl magnesium bromide (70 ml of 3N in diethyl ether, 0.21 mol) in dry THF (50 ml) at 0° C. The mixture was stirred at RT overnight. The reaction mixture was quenched with aq. HCl to pH 1 and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine, dried over MgSO4 and evaporated to give the title compound as an oil (22.3 g, 91%).

Workup

  1. customThe reaction mixture was quenched with aq. HCl to pH 1
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-ef0cc733a8df478796b9ce4083f35b76
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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