2-methylbenzenethiol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium (44 g, 1.92 mol) was added in small portions to 1.5 liter of absolute ethanol containing 217 g (1.75 mol) of thiocresol, with stirring, uinder nitrogen. After the addition was completed, 640 g (1.92 mol) of bromooctadecane was added, and the mixture was heated at reflux for 2 hours. The hot reaction mixture was filtered, and the ethanol was removed under reduced pressure. The residue was crystallized from heptane yielding 595 g (91%) of white crystals. mp 54°-55° C. After the addition the mixture was heated at reflux for 2 hours The hot reaction mixture was filtered the ethanol was removed under reduced pressure The residue was crystallized from heptane yielding 595 g (91%) of white crystals

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using an analogous procedure to that described in the first paragraph of the portion of Example 8 which is concerned with the preparation of starting materials, 3-chloro-4-fluoronitrobenzene was reacted with 2-toluenethiol. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated to give 2-chloro-4-nitrophenyl 2-tolyl sulphide in 31% yield. The reaction mixture was partitioned between ethyl acetate and water The organic phase was dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In ethanol (50 mL) was dissolved sodium metal (1.6 g, 66 mmol) at 23° C. 2-Methylbenzenethiol (8.1 mL, 68 mmol) was slowly added to this solution, followed by bromoacetaldehyde diethylacetal (9.50 mL, 63 mmol). The reaction mixture was stirred at reflux for 18 h. The solvent was then evaporated in vacuo and the residue was washed with H2O (100 mL) and extracted with ether (100 mL). The organic solution was dried (MgSO4), concentrated in vacuo and purified by distillation to afford the title compound (13.48 g, 82% yield): 1H NMR (400 MHz, CDCl3) δ ppm: 7.33 (1H, d, J=7.9 Hz), 7.16–7.08 (3H, m), 4.65 (1H, t, J=5.6 Hz), 3.66 (2H, q, J=7.0 Hz), 3.55 (2H, q, J=7.0 Hz), 3.09 (2H, d, J=5.6 Hz), 2.38 (3H, s), 1.20 (6H, t, J=7.0 Hz). LCMS (M+H)+ m/z 241 (t=2.65 min.). at reflux for 18 h The solvent was then evaporated in vacuo the residue was washed with H2O (100 mL) extracted with ether (100 mL) The organic solution was dried (MgSO4) concentrated in vacuo purified by distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of p-fluorobenzaldehyde (13.1 milliliters (hereinafter mL), 122 millimoles (hereinafter mmol) thiocresol (16.64 grams (hereinafter g), 122 mmol), formamide (15.0 mL, 445 mmol), and toluene (300 mL) were combined and heated to toluene reflux with azeotropic removal of H2O for 18 h. The cooled reaction was diluted with EtOAc (500 mL) and washed with satd aq Na2CO3(3×100 mL), satd aq NaCl (100 mL), dried (Na2SO4), and concentrated. The residue was triturated with petroleum ether, filtered and dried in vacuo to afford 28.50 g of the title compound as a white solid (85%). melting point (hereinafter mp)=119-120°. The cooled reaction washed with satd aq Na2CO3(3×100 mL) dried (Na2SO4) concentrated The residue was triturated with petroleum ether filtered dried in vacuo

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