Benzene → 2,3-Difluoro-4'-octyloxybiphenyl

HRID 36818

Reaction equation

HRID 36818 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1.C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[F:29][C:30]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOCC.C(O)C>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([C:34]2[CH:33]=[CH:32][CH:31]=[C:30]([F:29])[C:35]=2[F:36])=[CH:3][CH:4]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

8

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 145298p-Bromophenyl octyl etherHCID 2734333(2,3-Difluorophenyl)boronic acid

Product 1

HCID 184351832,3-Difluoro-4'-octyloxybiphenyl

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 4.2 g of the 4-bromo-1-n-octyloxybenzene, 0.5 g of tetrakis(triphenylphosphine) palladium(0), 53 ml of benzene, and 53 ml of an aqueous sodium carbonate solution (2 mol/liter), 26 ml of ethanol containing 3.0 g of 2,3-difluorophenyl boronic acid synthesized by the same method as in [1] in Example 1 was added dropwise, and then the solution thus formed was heated to reflux for 5 hours. After the solution was cooled, it was added with 200 ml of an ether to extract the product, washed with water and dried. The solvent was distilled off under a reduced pressure. The residue thus obtained was purified by a silica gel column chromatography using a mixed solvents of n-hexane and diethyl ether (10:2) to obtain 2.8 g of 4-n-octyloxy-2', 3'-difluorobiphenyl.

Workup

  1. additionwas added dropwise
  2. customthe solution thus formed
  3. temperaturewas heated
  4. temperatureto reflux for 5 hours
  5. temperatureAfter the solution was cooled
  6. extractionto extract the product
  7. washwashed with water
  8. customdried
  9. distillationThe solvent was distilled off under a reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-428b0d2d6c814cb8a67b68773bacfade
Source dataset
uspto-grants-1995_05
Patent number
US05417885

Linked notes

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