[3-bromo-4-(trifluoromethoxy)phenyl]methanol

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

Procedure: A mixture of 29.4 g (0.3 mol) of sulphuric acid, 50 ml of water and 2 ml of "Aliquat" 336 (tricaprylmethylammonium chloride) was added to a solution of 27 g (0.1 mol) of 3-bromo-4-trifluoromethoxybenzyl alcohol in 250 ml of methylene chloride at room temperature. Thereafter, 9.7 g (0.033 mol) of potassium dichromate were added to the reaction mixture, and the temperature was kept at approx. 25° C. for 2 hours by slight cooling. After 100 ml of water had been added to the mixture, the organic phase was separated off and the water was once again extracted by shaking with 100 ml of methylene chloride. The organic phases were washed twice with 100 ml of water, then once with 100 ml of saturated sodium bicarbonate solution, and once again with 100 ml of water, dried over sodium sulphate, and concentrated by evaporation in vacuo. The residue was distilled. In this manner, 20.4 g (75.8% of theory) of 3-bromo-4-trifluoromethoxybenzaldehyde were obtained as a colorless oil of boiling point 97° C./10 mm Hg. ##STR23## the organic phase was separated off the water was once again extracted The organic phases were washed twice with 100 ml of water once with 100 ml of saturated sodium bicarbonate solution, and once again with 100 ml of water, dried over sodium sulphate concentrated by evaporation in vacuo The residue was distilled

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

Procedure: A mixture of 29.4 g (0.3 mol) of sulphuric acid, 50 ml of water and 2 ml of "Aliquat" 336 (tricaprylmethylammonium chloride) was added to a solution of 27 g (0.1 mol) of 3-bromo-4-trifluoromethoxybenzyl alcohol in 250 ml of methylene chloride at room temperature. Thereafter, 9.7 g (0.033 mol) of potassium dichromate were added to the reaction mixture, and the temperature was kept at approx. 25° C. for 2 hours by slight cooling. After 100 ml of water had been added to the mixture, the organic phase was separated off and the water was once again extracted by shaking with 100 ml of methylene chloride. The organic phases were washed twice with 100 ml of water, then once with 100 ml of saturated sodium bicarbonate solution, and once again with 100 ml of water, dried over sodium sulphate, and concentrated by evaporation in vacuo. The residue was distilled. In this manner, 20.4 g (75.8% of theory) of 3-bromo-4-trifluoromethoxybenzaldehyde were obtained as a colorless oil of boiling point 97° C./10 mm Hg. ##STR23## the organic phase was separated off the water was once again extracted The organic phases were washed twice with 100 ml of water once with 100 ml of saturated sodium bicarbonate solution, and once again with 100 ml of water, dried over sodium sulphate concentrated by evaporation in vacuo The residue was distilled

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

Procedure: A mixture of 29.4 g (0.3 mol) of sulphuric acid, 50 ml of water and 2 ml of "Aliquat" 336 (tricaprylmethylammonium chloride) was added to a solution of 27 g (0.1 mol) of 3-bromo-4-trifluoromethoxybenzyl alcohol in 250 ml of methylene chloride at room temperature. Thereafter, 9.7 g (0.033 mol) of potassium dichromate were added to the reaction mixture, and the temperature was kept at approx. 25° C. for 2 hours by slight cooling. After 100 ml of water had been added to the mixture, the organic phase was separated off and the water was once again extracted by shaking with 100 ml of methylene chloride. The organic phases were washed twice with 100 ml of water, then once with 100 ml of saturated sodium bicarbonate solution, and once again with 100 ml of water, dried over sodium sulphate, and concentrated by evaporation in vacuo. The residue was distilled. In this manner, 20.4 g (75.8% of theory) of 3-bromo-4-trifluoromethoxybenzaldehyde were obtained as a colorless oil of boiling point 97° C./10 mm Hg. ##STR23## the organic phase was separated off the water was once again extracted The organic phases were washed twice with 100 ml of water once with 100 ml of saturated sodium bicarbonate solution, and once again with 100 ml of water, dried over sodium sulphate concentrated by evaporation in vacuo The residue was distilled

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (3-bromo-4-(trifluoromethoxy)phenyl)methanol 19.1 (6.78 g, 25 mmol) in 30 mL of DCM, was added DMF (0.5 mL) and thionyl bromide (2 mL, 26 mmol). The mixture was stirred at 23° C. for 4 hours. DCM (120 mL) was added to the reaction mixture, and the resulting mixture was washed with aqueous saturated NaHCO3. The organic layer was dried over Na2SO4 and concentrated to give 19.2 (8.3 g, 99% yield) as a yellow oil, which was used directly in the next step without further purification. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.74 (1H, d, J=2.0 Hz), 7.38-7.53 (2H, m), 4.53 (2H, d, J=5.6 Hz). the resulting mixture was washed with aqueous saturated NaHCO3 The organic layer was dried over Na2SO4 concentrated

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (3-bromo-4-(trifluoromethoxy)phenyl)methanol 19.1 (6.78 g, 25 mmol) in 30 mL of DCM, was added DMF (0.5 mL) and thionyl bromide (2 mL, 26 mmol). The mixture was stirred at 23° C. for 4 hours. DCM (120 mL) was added to the reaction mixture, and the resulting mixture was washed with aqueous saturated NaHCO3. The organic layer was dried over Na2SO4 and concentrated to give 19.2 (8.3 g, 99% yield) as a yellow oil, which was used directly in the next step without further purification. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.74 (1H, d, J=2.0 Hz), 7.38-7.53 (2H, m), 4.53 (2H, d, J=5.6 Hz). the resulting mixture was washed with aqueous saturated NaHCO3 The organic layer was dried over Na2SO4 concentrated

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (3-bromo-4-(trifluoromethoxy)phenyl)methanol 19.1 (6.78 g, 25 mmol) in 30 mL of DCM, was added DMF (0.5 mL) and thionyl bromide (2 mL, 26 mmol). The mixture was stirred at 23° C. for 4 hours. DCM (120 mL) was added to the reaction mixture, and the resulting mixture was washed with aqueous saturated NaHCO3. The organic layer was dried over Na2SO4 and concentrated to give 19.2 (8.3 g, 99% yield) as a yellow oil, which was used directly in the next step without further purification. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.74 (1H, d, J=2.0 Hz), 7.38-7.53 (2H, m), 4.53 (2H, d, J=5.6 Hz). the resulting mixture was washed with aqueous saturated NaHCO3 The organic layer was dried over Na2SO4 concentrated

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (3-bromo-4-(trifluoromethoxy)phenyl)methanol 19.1 (6.78 g, 25 mmol) in 30 mL of DCM, was added DMF (0.5 mL) and thionyl bromide (2 mL, 26 mmol). The mixture was stirred at 23° C. for 4 hours. DCM (120 mL) was added to the reaction mixture, and the resulting mixture was washed with aqueous saturated NaHCO3. The organic layer was dried over Na2SO4 and concentrated to give 19.2 (8.3 g, 99% yield) as a yellow oil, which was used directly in the next step without further purification. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.74 (1 H, d, J=2.0 Hz), 7.38-7.53 (2 H, m), 4.53 (2 H, d, J=5.6 Hz). the resulting mixture was washed with aqueous saturated NaHCO3 The organic layer was dried over Na2SO4 concentrated

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

Procedure: A mixture of 29.4 g (0.3 mol) of sulphuric acid, 50 ml of water and 2 ml of "Aliquat" 336 (tricaprylmethylammonium chloride) was added to a solution of 27 g (0.1 mol) of 3-bromo-4-trifluoromethoxybenzyl alcohol in 250 ml of methylene chloride at room temperature. Thereafter, 9.7 g (0.033 mol) of potassium dichromate were added to the reaction mixture, and the temperature was kept at approx. 25° C. for 2 hours by slight cooling. After 100 ml of water had been added to the mixture, the organic phase was separated off and the water was once again extracted by shaking with 100 ml of methylene chloride. The organic phases were washed twice with 100 ml of water, then once with 100 ml of saturated sodium bicarbonate solution, and once again with 100 ml of water, dried over sodium sulphate, and concentrated by evaporation in vacuo. The residue was distilled. In this manner, 20.4 g (75.8% of theory) of 3-bromo-4-trifluoromethoxybenzaldehyde were obtained as a colorless oil of boiling point 97° C./10 mm Hg. ##STR23## the organic phase was separated off the water was once again extracted The organic phases were washed twice with 100 ml of water once with 100 ml of saturated sodium bicarbonate solution, and once again with 100 ml of water, dried over sodium sulphate concentrated by evaporation in vacuo The residue was distilled