Sodium Carbonate → HCID 131727221, compound

HRID 2374119Notes

Reaction equation

HRID 2374119 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:22](=[O:25])([O-])[O-].[Na+].[Na+].[F:28][C:29]1[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=1B(O)OOCCCCCCCC>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:28][C:29]1[C:34]([F:35])=[C:33]([O:25][CH2:22][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH2:5][CH3:8])[CH:32]=[CH:31][C:30]=1[C:6]1[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:10][CH:9]=2)=[CH:4][CH:3]=[CH:2][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 69205003HCID 69205003, compoundHCID 87733077HCID 87733077, compound

Product 1

HCID 131727221HCID 131727221, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 4-bromo-4′-(6-hydroxyhexyloxy)biphenyl (3.30 g, 9.5 mmol) from step 2, a 2M-aqueous solution of sodium carbonate (40 ml) and tetrakis(triphenylphosphine)palladium(0) (0.28 g, 0.28 mmol) were mixed in DME (60 ml) under dry nitrogen at room temperature and 2,3-difluoro-octyloxyphenylboronic acid (3.25 g, 11.4 mmol) prepared as described in Example 1 step 4, was added. The stirred reaction mixture was heated under reflux under dry nitrogen overnight until g.l.c. and t.l.c. revealed a complete reaction. The product was extracted into DCM (2×150 ml) and washed with brine, water and dried (MgSO4). The solvent was removed under reduced pressure and the residue was purified by column chromatography [DCM-hexane, 1:1] and recrystallised from ethanol-hexane (1:4) to give a white powder.

Workup

  1. additionwas added
  2. customThe stirred reaction mixture
  3. temperaturewas heated
  4. temperatureunder reflux under dry nitrogen overnight until g.l.c
  5. customa complete reaction
  6. extractionThe product was extracted into DCM (2×150 ml)
  7. washwashed with brine, water
  8. dry with materialdried (MgSO4)
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified by column chromatography [DCM-hexane, 1:1]
  11. customrecrystallised from ethanol-hexane (1:4)
  12. customto give a white powder

Sources & evidence

ORD record
ord-d3759028654c4492841ed7f797b191a6
Source dataset
uspto-grants-2008_12
Patent number
US07462427B2

Reaction notes

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