Benzene → 1-Bromoacenaphthylene

HRID 1758283Notes

Reaction equation

HRID 1758283 reaction equation
[Br-:1].[K+].Br([O-])(=O)=O.[K+].S(=O)(=O)(O)O.[OH-].[K+].[CH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O.C(O)C>[Br:1][C:19]1[C:20]2=[C:20]3[C:19](=[CH:17][CH:16]=[CH:15]2)[CH:18]=[CH:17][CH:16]=[C:15]3[CH:18]=1

Participants

8

Reactant 5

HCID 241BenzeneHCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 253877Potassium BromideHCID 23673461Potassium Bromate

Product 1

HCID 6155531-Bromoacenaphthylene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 1 mol of 1,2,3,5-tetrabromoacenaphthlene (C12H6Br4) in 500 g of benzene and 2 mols of potassium bromide and 0.2 mols of potassium bromate in 600 g of water was placed in a three-necked flask and stirred vigorously in a dark place. Two mols of concentrated sulfuric acid diluted with an equal volume of water was added dropwise to the mixture under agitation at about 10° C. Following a 3-hr reaction, the benzene layer was washed sequentially with water, aqueous caustic soda (2%) and water, and dried with silica gel. A solution of the dried benzene was transferred to a three-necked flask where it was dehydrobromated with a solution of about 2 mols of potassium hydroxide in hot ethanol that was added dropwise through the dropping funnel. After the reaction, the benzene layer was washed with water and dried. After distilling benzene off under vacuum, the residue was washed thoroughly with hot acetone and dried to provide a bromoacenaphthylene condensate. It was estimated by elemental analysis that the condensate had a rational formula of (C12H3.7 Br2.9)1. GPC showed that it had a degree of condensation l in the range of from 2 to 5.

Workup

  1. customwas placed in a three-necked flask
  2. additionwas added dropwise to the mixture under agitation at about 10° C
  3. waitFollowing a 3-hr
  4. customreaction
  5. washthe benzene layer was washed sequentially with water, aqueous caustic soda (2%) and water
  6. customdried with silica gel
  7. customA solution of the dried benzene was transferred to a three-necked flask
  8. additionwas added dropwise through the dropping funnel
  9. customAfter the reaction
  10. washthe benzene layer was washed with water
  11. customdried
  12. distillationAfter distilling benzene off under vacuum
  13. washthe residue was washed thoroughly with hot acetone
  14. customdried

Sources & evidence

ORD record
ord-aad8e16d305f4f01a113acf1b9e02fbb
Source dataset
uspto-grants-1983_02
Patent number
US04373046

Reaction notes

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