Sodium Carbonate → HCID 18982655, compound

HRID 1440176Notes

Reaction equation

HRID 1440176 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[CH2:12]([S:19][C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:23]2[CH:24]=[CH:25][C:20]([S:19][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:21][CH:22]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 125212451-Bromo-4-(heptylsulfanyl)benzene

Product 1

HCID 18982655HCID 18982655, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Cyanophenylboronic acid (7 g, 0.0476 m) was stirred and refluxed for 60 hours under nitrogen with 4-n-heptylthiobromobenzene (12.4 g, 0.0433 m), TTPP (0.9 g, 0.000783 m), 2 molar aqueous sodium carbonate (41 mls). toluene (86 mls) and industrial methylated spirit (20.5 mls). The mixture was then separated and extincted with toluene (2×100 mls) washed with water (100 mls) and dried over magnesium sulphate. The solvents were then evaporated off to give a brown solid products which was purified by column chromatography and recrystallisation from industrial methylated spirit. 4-Cyano-4'-heptylthiobiphenyl was produced (4.1 g, 100% HPCL, 30% yield melting point 64.4° C.).

Workup

  1. customThe mixture was then separated
  2. washwashed with water (100 mls)
  3. dry with materialdried over magnesium sulphate
  4. customThe solvents were then evaporated off
  5. customto give a brown solid products which
  6. customwas purified by column chromatography and recrystallisation from industrial methylated spirit

Sources & evidence

ORD record
ord-a82715c95ecc440a89773611054da2dd
Source dataset
uspto-grants-1996_03
Patent number
US05498366

Reaction notes

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