Hydrochloric Acid → HCID 10681666, compound

HRID 325863Notes

Reaction equation

HRID 325863 reaction equation
BrC1[C:10]2[C:5](=[CH:6][C:7](F)=[CH:8][CH:9]=2)C(=O)C1.BrC1C2C(=CC=C(F)C=2)C(=O)C1.Br[CH:26]1[C:34]2[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=2)[C:28](=[O:36])[CH2:27]1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[C:5]1([CH:26]2[C:34]3[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=3)[C:28](=[O:36])[CH2:27]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 20462999HCID 20462999, compoundHCID 20463006HCID 20463006, compoundHCID 232936813-Bromo-6-fluoro-1-indanone

Product 1

HCID 10681666HCID 10681666, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a corresponding manner was made 3-bromo-6-fluoro-1-indanone melting at 62-64 degrees Centigrade, and 3-bromo-5-fluoro-1-indanone melting at 44-47 degrees Centigrade. To a solution of 113 grams of 3-bromo-6-chloro-1-indanone in 1400 milliliters of dry benzene were added over 10 minutes 230 grams of aluminiumchloride in portions. The reaction mixture was then refluxed for 3 hours, cooled and treated with crushed ice and concentrated hydrochloric acid. The organic phase was separated and extracted with 1 N sodium hydroxide and water, dried over anhydrous magnesium sulfate, treated with active carbon and concentrated in vacuo. The residue was taken up to 450 milliliters of hot n-hexane, cooled and filtered to give 96 grams of 3-phenyl-6-chloro-1-indanone melting at 84-92 degrees Centigrade.

Workup

  1. temperatureThe reaction mixture was then refluxed for 3 hours
  2. temperaturecooled
  3. customThe organic phase was separated
  4. extractionextracted with 1 N sodium hydroxide and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additiontreated with active carbon
  7. concentrationconcentrated in vacuo
  8. temperaturecooled
  9. filtrationfiltered

Sources & evidence

ORD record
ord-cc5c5c0fa6dd4aeb9dfd49e9efac0dd4
Source dataset
uspto-grants-1984_04
Patent number
US04443448

Reaction notes

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