p-Chlorothiophenol → HCID 18470318, compound

HRID 2228900Notes

Reaction equation

HRID 2228900 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][Br:9].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([SH:23])=[CH:19][CH:18]=1>CN(C)C=O>[Br:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][S:23][C:20]1[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 783091,7-Dibromoheptane

Product 1

HCID 18470318HCID 18470318, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To 1,7-dibromoheptane (23 g) and potassium carbonate (10 g) in dry dimethylformamide (100 ml) was added 4-chlorothiophenol (4.3 g) dropwise with stirring at 25° C. After 6 h, the mixture was filtered and the solvent removed under reduced pressure. Chromatography of the residue on silica gel using hexane as eluent gave 1-bromo-7-(4-chlorophenylthio)heptane (9.6 g). 1H-NMR (CDCl3) δ 1.2-1.55 (6H, m), 1.55-1.75 (2H, m), 1.8-2.0 (2H, m), 2.89 (2H, t), 3.40 (2H, t) and 7.2-7.4 (4H, m).

Workup

  1. filtrationthe mixture was filtered
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ea7363879e324375830db04f0cd35cfd
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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