[3,5-dichloro-4-(4-fluorophenyl)phenyl]methanol

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

Procedure: To a solution of 2,6-dichloro-4′-fluorobiphenyl-4-carboxylic acid (350 mg, 1.155 mmol) in THF (5 mL) was added 2M borane-methyl sulfide complex in THF (0.35 mL, 0.70 mmol) at room temperature. After 20 hours, the reaction was quenched with 2M HCl and water and was extracted twice with ethyl acetate. The organic layers were washed with brine containing some aqueous sodium bicarbonate, dried over sodium sulfate, combined and concentrated. The residue was purified on silica gel (COMBI FLASH 12 gm column, 100% DCM, then a gradient of 2-10% ethyl acetate/DCM) to give a single main band by TLC (65 mg) containing a 1:1 mixture of title intermediate and 3,5-dichlorobenzyl alcohol from the Step 1 bi-product impurity. The mixture was used directly in Step 3. the reaction was quenched with 2M HCl and water was extracted twice with ethyl acetate The organic layers were washed with brine containing some aqueous sodium bicarbonate dried over sodium sulfate concentrated The residue was purified on silica gel (COMBI FLASH 12 gm column, 100% DCM a gradient of 2-10% ethyl acetate/DCM) to give a single main band by TLC (65 mg) containing

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

Procedure: To a solution of 2,6-dichloro-4′-fluorobiphenyl-4-carboxylic acid (350 mg, 1.155 mmol) in THF (5 mL) was added 2M borane-methyl sulfide complex in THF (0.35 mL, 0.70 mmol) at room temperature. After 20 hours, the reaction was quenched with 2M HCl and water and was extracted twice with ethyl acetate. The organic layers were washed with brine containing some aqueous sodium bicarbonate, dried over sodium sulfate, combined and concentrated. The residue was purified on silica gel (COMBI FLASH 12 gm column, 100% DCM, then a gradient of 2-10% ethyl acetate/DCM) to give a single main band by TLC (65 mg) containing a 1:1 mixture of title intermediate and 3,5-dichlorobenzyl alcohol from the Step 1 bi-product impurity. The mixture was used directly in Step 3. the reaction was quenched with 2M HCl and water was extracted twice with ethyl acetate The organic layers were washed with brine containing some aqueous sodium bicarbonate dried over sodium sulfate concentrated The residue was purified on silica gel (COMBI FLASH 12 gm column, 100% DCM a gradient of 2-10% ethyl acetate/DCM) to give a single main band by TLC (65 mg) containing

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

Procedure: To a solution of 2,6-dichloro-4′-fluorobiphenyl-4-carboxylic acid (350 mg, 1.155 mmol) in THF (5 mL) was added 2M borane-methyl sulfide complex in THF (0.35 mL, 0.70 mmol) at room temperature. After 20 hours, the reaction was quenched with 2M HCl and water and was extracted twice with ethyl acetate. The organic layers were washed with brine containing some aqueous sodium bicarbonate, dried over sodium sulfate, combined and concentrated. The residue was purified on silica gel (COMBI FLASH 12 gm column, 100% DCM, then a gradient of 2-10% ethyl acetate/DCM) to give a single main band by TLC (65 mg) containing a 1:1 mixture of title intermediate and 3,5-dichlorobenzyl alcohol from the Step 1 bi-product impurity. The mixture was used directly in Step 3. the reaction was quenched with 2M HCl and water was extracted twice with ethyl acetate The organic layers were washed with brine containing some aqueous sodium bicarbonate dried over sodium sulfate concentrated The residue was purified on silica gel (COMBI FLASH 12 gm column, 100% DCM a gradient of 2-10% ethyl acetate/DCM) to give a single main band by TLC (65 mg) containing