tert-butylsulfanylbenzene

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

Procedure: In the drybox, 51.0 mg (0.226 mmol) of (Me2CH)PH(O)(1-NMe2-4-Me—C6H3) from Example 32, 34.0 mg (0.151 mmol) of Pd(OAc)2 and 4.0 ml of toluene were loaded into a reactor (20 ml) equipped with a magnetic stir bar. The resulting mixture was stirred at room temperature for 1 h. Next, 216.0 mg (2.25 mmol) of NaOtBu, 314.0 mg (2.0 mmol) of PhBr and 135 mg (1.5 mmol) of HS-t-Bu were added into the mixture above, The resulting mixture was refluxed for 18 h. The reaction mixture was then cooled to room temperature, chromatographed on silicon gel using ethyl acetate/hexane (5% volume ratio) as eluant. The eluate was concentrated by rotary evaporation followed by high vacuum to yield 126 mg (51% yield) of t-butyl phenyl sulfide. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ7.43-7.42 (m, 2H), 7.22-7.19 (m, 3H), 1.17 (s, 9H) ppm. 13C NMR (125 MHz, CDCl3): δ137.4, 132.7, 128.5, 128.3, 30.9 ppm. (20 ml) equipped with a magnetic stir bar was refluxed for 18 h The reaction mixture was then cooled to room temperature chromatographed on silicon gel The eluate was concentrated by rotary evaporation

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

Procedure: In the drybox, 52.0 mg (0.184 mmol) of (Me2CH)PH(O)(2,4-(MeO)2C6H3) from Example 34, 34.0 mg (0.151 mmol) of Pd(OAc)2 and 14.0 ml of toluene were loaded into a reactor (20 ml) equipped with a magnetic stir bar. The resulting mixture was stirred at room temperature for 1 h. Next, 576.0 mg (6.0 mmol) of NaOtBu, 816.0 mg (4.0 mmol) of PhI and 360 mg (4.0 mmol) of HS-t-Bu were added into the mixture above, The resulting mixture was refluxed for 3 days. The reaction mixture was then cooled to room temperature, chromatographed on silicon gel using ethyl acetate/hexane (5% volume ratio) as eluant. The eluate was concentrated by rotary evaporation followed by high vacuum to yield 190 mg (29% yield) of t-butyl phenyl sulfide. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ7.43-7.42 (m, 2H), 7.22-7.19 (m, 3H), 1.17 (s, 9H) ppm. 13C NMR (125 MHz, CDCl3): δ137.4, 132.7, 128.5, 128.3, 30.9 ppm. (20 ml) equipped with a magnetic stir bar was refluxed for 3 days The reaction mixture was then cooled to room temperature chromatographed on silicon gel The eluate was concentrated by rotary evaporation

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

Procedure: In the drybox, 133.7 mg (0.75 mm) of (Me3C)2PH(S), 170.0 mg (0.75 mm) of Pd(OAc)2 and 10.0 mL of DMSO were loaded into a reactor (50 mL) equipped with a magnetic stir bar. The resulting mixture was stirred at room temperature for 12 h. Next, 2.0 g (17.7 mm) of chlorobenzene, 1.35 g (15.0 mm) of t-butylthiol, and 2.16 g (22.5 mm) of NaO—tBu were added into the reactor. The resulting mixture was refluxed for 12 h. The reaction mixture was then cooled to room temperature, chromatographed on silicon gel using t-butylmethylether/hexane (1% volume ratio) as eluant. The eluate was concentrated by rotary evaporation followed by high vacuum to yield 812 mg (33% yield) of t-butyl phenyl sulfide. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ7.4-7.2 (m, 5H), 1.17 (s, 9H) ppm. 13C NMR (125 MHz, CDCl3): δ137.4, 132.7, 128.5, 128.3, 45.6, 30.9 ppm. HRMS: Calcd for C10H15S(M++H): 167.0894. Found: 167.0888. (50 mL) equipped with a magnetic stir bar The resulting mixture was refluxed for 12 h The reaction mixture was then cooled to room temperature chromatographed on silicon gel The eluate was concentrated by rotary evaporation

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

Procedure: To a mixture of 55 grams (0.5 mole) of thiophenol and 51 grams of boron trifluoride-phosphoric acid complex was slowly added, with stirring and cooling, 34 grams (0.6 mole) of isobutylene at 0° C. After addition was complete the mixture was stirred at 0° C. for two hours. The organic layer was separated from the catalyst layer and added to 200 ml of toluene. The toluene layer was distilled in a one-foot packed column to give 78 grams of tert-Butyl Phenyl Sulfide, b.p. 55°/3.0 mm (yield 94%). The nmr spectrum agreed with the proposed structure. was slowly added cooling at 0° C After addition was stirred at 0° C. for two hours The organic layer was separated from the catalyst layer added to 200 ml of toluene The toluene layer was distilled in a one-foot