3-(4-Bromophenyl)propionic acid → 1-Indanone, 6-bromo-

HRID 1503369Notes

Reaction equation

HRID 1503369 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>O=S(Cl)Cl.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][CH2:9][C:10]2=[O:12])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 27356093-(4-Bromophenyl)propionic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1397781-Indanone, 6-bromo-Yield 473.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 3-(4-bromophenyl)propanoic acid (26 g, 12 mmol) in SOCl2 (50 mL) was refluxed overnight, the mixture was concentrated, then added to AlCl3 (80 g, 61 mmol) in DCM (100 mL), the mixture was stirred at room temperature overnight. The mixture was quenched with HCl aqueous, extracted with DCM, washed with brine, dried over Na2SO4, concentrated to give 6-bromo-indan-1-one (12 g, 48%). 1H-NMR (CD3OD): 2.65 (m, 2H), 3.06 (m, 2H), 7.31 (m, 1H), 7.62 (m, 1H), 7.80 (m, 1H).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationthe mixture was concentrated
  3. customThe mixture was quenched with HCl aqueous
  4. extractionextracted with DCM
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-05422a00136c433bb31595fb5e36e805
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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