Ethylene → 8-Bromo-1,2,3,4-tetrahydronaphthalen-2-one

HRID 728074Notes

Reaction equation

HRID 728074 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13](Cl)=[O:14].[CH2:16]=[CH2:17]>C(Cl)Cl>[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:7]=1[CH2:12][C:13](=[O:14])[CH2:17][CH2:16]2

Participants

5

Reactant 3

HCID 6325EthyleneHCID 41383862-Bromophenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 41361878-Bromo-1,2,3,4-tetrahydronaphthalen-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

83.5 g of aluminum chloride (0.63 mmol) were introduced into 1.8 liters of methylene chloride at 0°-+5° C. 105 g (0.49 mole) of 2-bromophenyl-acetyl chloride (dissolved in 200 ml of methylene chloride) were added dropwise at 0°-+5° C. over 30 minutes. After stirring for 30 minutes at 0°-+5° C., 50 g of ethylene were passed in at such a rate that the reaction temperature did not exceed +10° C. The mixture was stirred for a further 2 hours at 20°-+25° C. The aluminum complex was decomposed by careful addition of 500 ml of ice water, the phases were separated, and the aqueous phase was extracted with 250 ml of methylene chloride. The title compound was obtained from the dried methylene chloride phase in a yield of 109 g as a yellow oil (content according to GC 97%) and employed without further purification.

Workup

  1. customdid not exceed +10° C
  2. stirringThe mixture was stirred for a further 2 hours at 20°-+25° C
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with 250 ml of methylene chloride

Sources & evidence

ORD record
ord-466ce25420ef495b813c28d665abd854
Source dataset
uspto-grants-1991_09
Patent number
US05047422

Reaction notes

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