ethylsulfanylbenzene

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

Conditions: temp:55.01; pressure:0.00; stir:

Procedure: dtbpy: The mixture of product (110 mg, 83% yield, ortho/meta + para = 0.29); meta- and para- isomers (5b+5bʹ) were obtained by further purification of the crude mixture by GPC (77 mg, 58% yield), colorless oil;

Conditions: temp:55.01; pressure:0.00; stir:

Procedure: Ligand 3f: The mixture of product (95 mg, 72% yield, ortho/meta + para = >30); ortho-borylated product 4b was obtained by further purification of the crude mixture by GPC (89 mg, 67% yield), white solid (mp. 48-50 oC)

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

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 11.52 g (63 mmoles) of phenylthio(trimethyl)silane, 22 ml of hexamethylphosphoric triamide and 18.8 ml (250 mmoles) of ethyl bromide was heated in a bath at 40° C. for 2 hours after which the conversion was complete. A solid formed in the reaction mixture and heating was continued for 1 hour after which the mixture was poured into a mixture of 150 ml of ethyl acetate and 50 ml of water. The ethyl acetate layer was separated and washed sequentially twice with 50 ml of water, 50 ml of a saturated sodium bicarbonate solution and twice with 25 ml of water. The combined water layers were extracted three times with 25 ml of ethyl acetate and the combined organic phases were washed twice with 25 ml of water, dried and evaporated to dryness. The residue was vacuum distilled to obtain 7.25 g (83% yield) of ethyl phenyl sulfide with a boiling point of 81.5°-84° C./14 mm Hg and a refractive index of nD25 =1.5632. A solid formed in the reaction mixture heating The ethyl acetate layer was separated washed sequentially twice with 50 ml of water, 50 ml of a saturated sodium bicarbonate solution and twice with 25 ml of water The combined water layers were extracted three times with 25 ml of ethyl acetate the combined organic phases were washed twice with 25 ml of water dried evaporated to dryness distilled

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Aluminum chloride (2 g, 15 mmol) was suspended in 8 mL 1,2-dichloroethane and the solution was cooled to 5° C. Dimethoxymethane (0.69 mL, 7.8 mmol) over 10 min. Ethylphenylsulfide (0.88 mL, 6.5 mmol) was added and the mixture was warmed to rt. After 15 h ice water was added and the mixture was extracted with methylene chloride (3×). The combined organic fractions were dried over magnesium sulfate and concentrated. The crude material was used directly in the next step. the mixture was warmed to rt the mixture was extracted with methylene chloride (3×) The combined organic fractions were dried over magnesium sulfate concentrated