Sodium Carbonate → 2-(4-Dodecyloxyphenyl)-6-(4-nonylphenyl)benzothiazole

HRID 1243267Notes

Reaction equation

HRID 1243267 reaction equation
Br[C:2]1[CH:29]=[CH:28][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:11][CH:10]=3)[S:8][C:4]=2[CH:3]=1.[CH2:30]([C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].C(=O)([O-])[O-].[Na+].[Na+]>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.COCCOC>[CH2:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[S:8][C:4]3[CH:3]=[C:2]([C:42]4[CH:41]=[CH:40][C:39]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:44][CH:43]=4)[CH:29]=[CH:28][C:5]=3[N:6]=2)=[CH:10][CH:11]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 4589192B-(4-Nonylphenyl)boronic acidHCID 219245176-Bromo-2-(4-dodecyloxyphenyl)benzothiazole

Product 1

HCID 219245242-(4-Dodecyloxyphenyl)-6-(4-nonylphenyl)benzothiazoleYield 74.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of tetrakis(triphenylphosphine)palladium(0) (0.30 g, 0.26×10−3 mol), 6-bromo-2-(4-dodecyloxyphenyl)benzothiazole (2.50 g, 5.27×10−3 mol), 4-nonylbenzene boronic acid (1.57 g, 6.33×10−3 mol), 2M sodium carbonate solution (25 cm3) and 1,2-dimethoxyethane (100 cm3). The reaction mixture was heated under reflux overnight. The cooled reaction mixture was extracted with dichloromethane (2×100 cm3) and the combined organic layers were washed with brine (2×100 cm3) and dried (MgSO4). After filtration the solvent was removed under reduced pressure and the residue was purified by column chromatography [silica gel, dichloromethane: hexane 1:1] followed by recrystallisation from ethanol to yield 2.35 g (74.5%) of the desired product.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. customThe cooled reaction mixture
  4. extractionwas extracted with dichloromethane (2×100 cm3)
  5. washthe combined organic layers were washed with brine (2×100 cm3)
  6. dry with materialdried (MgSO4)
  7. filtrationAfter filtration the solvent
  8. customwas removed under reduced pressure
  9. customthe residue was purified by column chromatography [silica gel, dichloromethane: hexane 1:1]
  10. customfollowed by recrystallisation from ethanol

Sources & evidence

ORD record
ord-b9019a6422c344968f2a374246573bbb
Source dataset
uspto-grants-2006_10
Patent number
US07118787B2

Reaction notes

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