Sodium Chloride → 5-Bromo-1-indanone

HRID 1646548Notes

Reaction equation

HRID 1646548 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+]>C(O)(=O)C>[Br:12][C:9]1[CH:8]=[C:7]2[C:6](=[CH:11][CH:10]=1)[C:4](=[O:5])[CH2:3][CH2:2]2

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 957904'-Bromo-3-chloropropiophenoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5206955-Bromo-1-indanoneYield 42.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-(3-Chloropropanoyl)bromobenzene (ex. Lancaster) (24.7 g) added to aluminium chloride (100 g) and sodium chloride (25 g) at 180°. After 30 minutes at 180°-220° the mixture was poured onto ice and treated with acetic acid (30 ml). The resultant product was collected and taken up in ether, the organic solution was dried and concentrated and the residue recrystallised from methanol to give 5-bromoindan-1-one (9 g).

Workup

  1. additionAfter 30 minutes at 180°-220° the mixture was poured onto ice
  2. customThe resultant product was collected
  3. customthe organic solution was dried
  4. concentrationconcentrated
  5. customthe residue recrystallised from methanol

Sources & evidence

ORD record
ord-a9596729fcc543ccafd064915a684ca7
Source dataset
uspto-grants-1993_01
Patent number
US05180737

Reaction notes

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