Hydrogen Bromide → 2-Bromo-5-chloro-2,3-dihydro-1H-inden-1-one

HRID 46626

Reaction equation

HRID 46626 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7]2.Br.OS([O-])=O.[Na+]>C(O)(=O)C.O>[Br:1][CH:8]1[CH2:7][C:6]2[C:10](=[CH:11][CH:12]=[C:4]([Cl:3])[CH:5]=2)[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 24408BromineHCID 1425995-Chloro-1-indanoneHCID 23665763Sodium Bisulfite

Product 1

HCID 113340692-Bromo-5-chloro-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of 37.9 g (0.237 mole) of bromine in 120 ml of glacial acetic acid is slowly added dropwise, whilst stirring, to a solution of 40.0 g (0.237 mole) of 5-chloro-1-indanone in 590 ml of glacial acetic acid, to which 0.2 ml of 48% strength aqueous hydrobromic acid has been added. The mixture is stirred for a further 2 hours and the reaction solution is poured into 1 l of water, to which 2.5 g of NaHSO3 have been added. The product, which initially precipitates in the viscous form, becomes crystalline after stirring for a relatively long time. The crude product is filtered off (melting point 69°-76° C.), washed with water and recrystallized from petroleum ether. The pure 2-bromo-5-chloro-1-indanone melts at 89°-90° C.

Workup

  1. additionhas been added
  2. additionhave been added
  3. customThe product, which initially precipitates in the viscous form
  4. stirringafter stirring for a relatively long time
  5. filtrationThe crude product is filtered off (melting point 69°-76° C.)
  6. washwashed with water
  7. customrecrystallized from petroleum ether

Sources & evidence

ORD record
ord-bda33951a12b4d7bb06da4765a8bf10e
Source dataset
uspto-grants-1979_11
Patent number
US04174397

Linked notes

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