Sodium Carbonate → HCID 18982655, compound

HRID 1707208Notes

Reaction equation

HRID 1707208 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 end extincted with toluene (2×10 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 end
  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-fbf2878a83214f49ba4bde529b07025e
Source dataset
uspto-grants-1994_10
Patent number
US05352381

Reaction notes

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