1-Bromooctane → 4,4'-Dioctyloxy-3,3'-difluorobiphenyl

HRID 1646833Notes

Reaction equation

HRID 1646833 reaction equation
[CH2:1]([O:9][C:10]1[C:11]([F:25])=[C:12](C2C(O)=CC=CC=2F)[C:13](O)=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[F:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][C:32]=1[O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].C(OC1C=CC(Br)=CC=1F)C1C=CC=CC=1.BrCCCCCCCC.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:29]2[CH:30]=[CH:31][C:32]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[C:27]([F:26])[CH:28]=2)=[CH:12][C:11]=1[F:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 5

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 10611926Boronic acid, [3-fluoro-4-(octyloxy)phenyl]-HCID 187574911-(Benzyloxy)-4-bromo-2-fluorobenzeneHCID 197999174'-Octyloxy-3,3'-difluorobiphenol

Product 1

HCID 197998654,4'-Dioctyloxy-3,3'-difluorobiphenyl

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4'-octyloxy-3,3'-difluorobiphenol (0.1 mol, obtained by coupling 3-fluoro-4-octyloxyphenyl boronic acid with 4-benzyloxy-3-fluoro-brombenzene followed by hydrogenolytic cleavage of the benzylic ether), 1-bromooctane (0.12 mol), potassium carbonate (30 g) and butanone (125 ml) is heated under reflux and stirred for 20 hrs. After cooling the reaction mixture is filtered and the filtrate evaporated off, distillation under reduced pressure affords the required product, m.p. 84°.

Workup

  1. customobtained
  2. temperatureis heated
  3. temperatureunder reflux
  4. temperatureAfter cooling the reaction mixture
  5. filtrationis filtered
  6. customthe filtrate evaporated off
  7. distillationdistillation under reduced pressure

Sources & evidence

ORD record
ord-96a5762e0ede4c1c80364ac093936b53
Source dataset
uspto-grants-1993_01
Patent number
US05182047

Reaction notes

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