Sodium Carbonate → HCID 131727220, compound

HRID 2374116Notes

Reaction equation

HRID 2374116 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][CH:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:31][C:32]1[C:37]([F:38])=[C:36]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:35]=[CH:34][C:33]=1B(O)O>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>[CH3:24][CH:17]([CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:16][CH2:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[C:4]([C:33]3[CH:34]=[CH:35][C:36]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[C:37]([F:38])[C:32]=3[F:31])=[CH:3][CH:2]=[CH:7][CH:6]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10850744(2,3-Difluoro-4-(octyloxy)phenyl)boronic acidHCID 18676612HCID 18676612, compound

Product 1

HCID 131727220HCID 131727220, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Bromo-4′-(3,7-dimethyloctyloxy)biphenyl (0.80 g, 2.0 mmol) from step 1, an aqueous solution 2M-sodium carbonate (40 ml) and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.12 mmol) were mixed in DME (60 ml) under dry nitrogen at room temperature and 2,3-difluoro-4-octyloxyphenylboronic acid (0.62 g, 2.2 mmol), prepared as described in Example 1 step 4, was added. The stirred reaction mixture was heated overnight under reflux under dry nitrogen 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 [ether-hexane, 3:1] and recrystallised from ethanol to give the desired compound as white crystals.

Workup

  1. additionwas added
  2. customThe stirred reaction mixture
  3. temperaturewas heated overnight
  4. temperatureunder reflux under dry nitrogen 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 [ether-hexane, 3:1]
  11. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-d8baa031a00441918d8dbd1680ffebaa
Source dataset
uspto-grants-2008_12
Patent number
US07462427B2

Reaction notes

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