1,3-Dichloro-5-(trifluoromethyl)benzene

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

Procedure: The title compound was prepared as described in Example 159 substituting 1,3-dichloro-5-(trifluoromethyl)benzene for 1-chloro-3-methoxy-5-(trifluoromethyl)benzene.

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

Procedure: Beginning with 3,5-dichlorobenzotrifluoride (500 mg, 2.32 mmol) and piperazine (1 g, 11.6 mmol), 320 mg of the title compound was recovered by the procedure described in Example 1.

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

Procedure: The title compound was prepared as described in Example 159 substituting 1,3-dichloro-5-(trifluoromethyl)benzene for 1-chloro-3-methoxy-5-(trifluoromethyl)benzene.

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

Procedure: 3,5-Dichlorobenzotrifluoride (1.10 g, 5.1 mmol) and cyclopropylboronic acid (440 mg, 5.1 mmol) were reacted using K3PO4 (3.8 g, 17.9 mmol), tricyclohexylphosphine (145 mg, 0.51 mmol), Pd(OAc)2 (60 mg, 0.27 mmol) as described in example 100 to give 1-chloro-3-cyclopropyl-5-trifluoromethyl-benzene (980 mg, 87%) after purification by flash chromatography on silica gel.

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

Procedure: 3,5-Dichlorobenzotrifluoride (1.10 g, 5.1 mmol) and cyclopropylboronic acid (440 mg, 5.1 mmol) were reacted using K3PO4 (3.8 g, 17.9 mmol), tricyclohexylphosphine (145 mg, 0.51 mmol), Pd(OAc)2 (60 mg, 0.27 mmol) as described in example 100 to give 1-chloro-3-cyclopropyl-5-trifluoromethyl-benzene (980 mg, 87%) after purification by flash chromatography on silica gel.

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

Procedure: Beginning with 3,5-dichlorobenzotrifluoride (500 mg, 2.32 mmol) and piperazine (1 g, 11.6 mmol), 320 mg of the title compound was recovered by the procedure described in Example 1.

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

Procedure: Beginning with 3,5-dichlorobenzotrifluoride (500 mg, 2.32 mmol) and piperazine (1 g, 11.6 mmol), 320 mg of the title compound was recovered by the procedure described in Example 1.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2M n-BuLi solution (5.8 mL, 11.6 mmol) was added to a −78° C. THF solution (60 mL) of 1,3-dichloro-5-(trifluoromethyl)benzene (2.5 g, 11.6 mmol). After 45 min neat DMF (0.39 mL, 5.0 mmol) was added, and the resulting solution was allowed to warm to 0° C. gradually, quenched with NH4Cl solution, and extracted with diethyl ether. The combined extracts were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound. quenched with NH4Cl solution extracted with diethyl ether The combined extracts were dried (Na2SO4) concentrated purified via column chromatography

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

Procedure: Beginning with 3,5-dichlorobenzotrifluoride (500 mg, 2.32 mmol) and piperazine (1 g, 11.6 mmol), 320 mg of the title compound was recovered by the procedure described in Example 1.

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

Procedure: The title compound was prepared as described in Example 159 substituting 1,3-dichloro-5-(trifluoromethyl)benzene for 1-chloro-3-methoxy-5-(trifluoromethyl)benzene.