Sodium Carbonate → HCID 131727222, compound

HRID 2374121Notes

Reaction equation

HRID 2374121 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][O:21][CH2:22][CH:23]3[CH2:26][CH2:25][CH2:24]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:33][C:34]1[C:39]([F:40])=[C:38]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH:37]=[CH:36][C:35]=1B(O)O>COCCOC.[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>[CH:23]1([CH2:22][O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([C:5]3[C:4]([C:35]4[CH:36]=[CH:37][C:38]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[C:39]([F:40])[C:34]=4[F:33])=[CH:3][CH:2]=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)[CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10850744(2,3-Difluoro-4-(octyloxy)phenyl)boronic acidHCID 69206624HCID 69206624, compound

Product 1

HCID 131727222HCID 131727222, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Bromo-4′-[6-(cyclobutylmethoxy)hexyloxy]biphenyl (0.70 g, 1.7 mmol) from step 3 and a 2M-aqueous solution of sodium carbonate (40 ml) were mixed in DME (60 ml) and with tetrakis(triphenylphosphine)-palladium(0) (0.12 g, 0.12 mmol) under dry nitrogen; to which 2,3-difluoro-4-octyloxyphenylboronic acid (prepared as described in Example 1 step 4) (0.58 g, 2.0 mmol) was added. The stirred reaction mixture was heated under reflux overnight. The product was extracted into DCM 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, 1:5] and recrystallised from hexane to give white crystals.

Workup

  1. customThe stirred reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux overnight
  4. extractionThe product was extracted into DCM
  5. washwashed with brine, water
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography [DCM-hexane, 1:5]
  9. customrecrystallised from hexane
  10. customto give white crystals

Sources & evidence

ORD record
ord-ee36e6bd08884775b3db7e80d2e73cce
Source dataset
uspto-grants-2008_12
Patent number
US07462427B2

Reaction notes

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