2-(2-chlorophenyl)acetaldehyde

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

Procedure: By substituting an equimolar amount of o-chlorophenylacetaldehyde for 2,4-dichloro-6-phenylmethoxybenzaldehyde in step C of Example 1 and following Steps C through F there is obtained a corresponding amount of the title compound.

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

Procedure: By substituting an equimolar amount of o-chlorophenylacetaldehyde for 2,4-dichloro-6-phenylmethoxybenzaldehyde in step C of Example 1 and following Steps C through F there is obtained a corresponding amount of the title compound.

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

Procedure: By substituting an equimolar amount of o-chlorophenylacetaldehyde for 2,4-dichloro-6-phenylmethoxybenzaldehyde in step C of Example 1 and following Steps C through F there is obtained a corresponding amount of the title compound.

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

Procedure: A mixture of 1-chloro-2-(2-methoxyvinyl)benzene (2.4 g, 14 mmol) in a solution of 4.0M hydrogen chloride in 1,4-dioxane (36 mL) was stirred for 30 minutes at room temperature. The reaction mixture was then diluted with diethyl ether (100 mL) and treated with saturated aqueous sodium bicarbonate solution (60 mL)—caution: gas evolution. The organic layer was separated, washed with a sodium phosphate buffer (1.0M solution in water, pH=8, 2×40 mL), dried over sodium sulfate, filtered, and evaporated in vacuo to afford the title compound as a colorless oil (2.0 g, 90%), which was used in the next step without further purification. The organic layer was separated washed with a sodium phosphate buffer (1.0M solution in water, pH=8, 2×40 mL) dried over sodium sulfate filtered evaporated in vacuo

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

Procedure: By substituting an equimolar amount of o-chlorophenylacetaldehyde for 2,4-dichloro-6-phenylmethoxybenzaldehyde in step C of Example 1 and following Steps C through F there is obtained a corresponding amount of the title compound.

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

Procedure: The process of Example 3 is repeated using o-chlorophenylacetaldehyde to prepare ethyl 2-isopropyl-4-(o-chlorophenyl)-3-butenoate, which is hydrolyzed (potassium hydroxide-water/methanol) to the acid, 2-isopropyl-4-(o-chlorophenyl)-3-butenoic acid. The acid is reacted with m-phenoxybenzyl bromide as in Example 1 to yield m-phenoxybenzyl 2-isopropyl-4-(o-chlorophenyl)-3-butenoate. MS m/e 420 (M+).

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

Procedure: The process of Example 3 is repeated using o-chlorophenylacetaldehyde to prepare ethyl 2-isopropyl-4-(o-chlorophenyl)-3-butenoate, which is hydrolyzed (potassium hydroxide-water/methanol) to the acid, 2-isopropyl-4-(o-chlorophenyl)-3-butenoic acid. The acid is reacted with m-phenoxybenzyl bromide as in Example 1 to yield m-phenoxybenzyl 2-isopropyl-4-(o-chlorophenyl)-3-butenoate. MS m/e 420 (M+).

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

Procedure: The title compound was prepared from [2-amino-3-(trifluoromethyl)phenyl]-(3-hydroxy-phenyl)methanone and (2-chloro-phenyl)-acetaldehyde following the procedure of Example 457: MS (ES) m/z 397.9; HRMS: calcd for C22H13ClF3NO+H+, 400.07105; found (ESI, [M+H]+), 400.0706.

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

Procedure: The title compound is prepared as described in Example 12 (Procedure B) for 3-thiophenylacetaldehyde but using 2-chlorophenyl-ethanol. The title compound: ES-MS: 152.9 [M−H]−; single peak at tR=3.82 min (System 2); Rf=0.70 (CH2Cl2/Et2O, 95/5). The title compound is prepared

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

Procedure: The title compound is prepared as described in Example 12 (Procedure B) for 4-(5-thiophen-3-yl-thiazol-2-yl-amino)-phenol but starting from (2-chlorophenyl)-acetaldehyde. The title compound: ES-MS: 303.0 [M+H]+; single peak at tR=3.59 min (System 2); Rf=0.21 (CH2Cl2/MeOH, 95/5). The title compound is prepared

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

Procedure: A mixture of 1-chloro-2-(2-methoxyvinyl)benzene (2.4 g, 14 mmol) in a solution of 4.0M hydrogen chloride in 1,4-dioxane (36 mL) was stirred for 30 minutes at room temperature. The reaction mixture was then diluted with diethyl ether (100 mL) and treated with saturated aqueous sodium bicarbonate solution (60 mL)—caution: gas evolution. The organic layer was separated, washed with a sodium phosphate buffer (1.0M solution in water, pH=8, 2×40 mL), dried over sodium sulfate, filtered, and evaporated in vacuo to afford the title compound as a colorless oil (2.0 g, 90%), which was used in the next step without further purification. The organic layer was separated washed with a sodium phosphate buffer (1.0M solution in water, pH=8, 2×40 mL) dried over sodium sulfate filtered evaporated in vacuo

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

Procedure: By substituting an equimolar amount of o-chlorophenylacetaldehyde for 2,4-dichloro-6-phenylmethoxybenzaldehyde in step C of Example 1 and following Steps C through F there is obtained a corresponding amount of the title compound.