Potassium Iodide → 4-Bromo-4'-decyloxybiphenyl

HRID 651312

Reaction equation

HRID 651312 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(C1C=CC(C2C=CC(OCCCCCCCCCC)=CC=2)=CC=1)#N>CC(=O)CC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 950934-Bromo-4'-hydroxybiphenylHCID 112405[1,1'-Biphenyl]-4-carbonitrile, 4'-(decyloxy)-

Product 1

HCID 106680514-Bromo-4'-decyloxybiphenyl

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Quantities: 4-bromo-4′-hydroxybiphenyl (67) (20.00 g, 0.08 mol), 1-bromodecane (22.12 g, 0.10 mol), anhydrous potassium carbonate (57.10 g, 0.413 mol), potassium iodide (trace), butanone (500 ml). The experimental procedure was as described for the preparation of compound 57. The cooled mixture of product and inorganic salts was filtered off and washed carefully with dilute hydrochloric acid to remove the potassium carbonate. The white product was then washed with water until acid-free and heated under reflux with a minimum volume of ethanol to remove traces of 1-bromodecane. The product was filtered off, washed with cold ethanol and dried in vacuo to yield colourless crystals.

Workup

  1. additionThe cooled mixture of product and inorganic salts
  2. filtrationwas filtered off
  3. washwashed carefully with dilute hydrochloric acid
  4. customto remove the potassium carbonate
  5. washThe white product was then washed with water until acid-free and
  6. temperatureheated
  7. temperatureunder reflux with a minimum volume of ethanol
  8. customto remove traces of 1-bromodecane
  9. filtrationThe product was filtered off
  10. washwashed with cold ethanol
  11. customdried in vacuo
  12. customto yield colourless crystals

Sources & evidence

ORD record
ord-bba584ad74224236a3aa681dde7db484
Source dataset
uspto-grants-2001_08
Patent number
US06278028B1

Linked notes

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