bis(4-bromophenyl)methanol

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

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

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

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

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

Procedure: To a stirring solution of bis(4-bromophenyl)methanol (0.060 mmol) in CH2Cl2 (0.3 mL) was added thionyl chloride (40 μL, 0.60 mmol) and the reaction mixture was stirred for 48 h. The reaction was evaporated to dryness under a stream of N2 and the crude product redissolved in acetonitrile (1.0 mL). 1-Boc-piperazine (22.3 mg, 0.12 mmol) was added and the reaction mixture was refluxed for 4 h. The reaction mixture was concentrated under reduced pressure, redissolved in CH2Cl2 and passed through a short pad of SiO2, providing the 1-Boc-4-diphenylmethylpiperazine. The reaction was evaporated to dryness under a stream of N2 the crude product redissolved in acetonitrile (1.0 mL) the reaction mixture was refluxed for 4 h The reaction mixture was concentrated under reduced pressure redissolved in CH2Cl2

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

Procedure: To a stirring solution of bis(4-bromophenyl)methanol (0.060 mmol) in CH2Cl2 (0.3 mL) was added thionyl chloride (40 μL, 0.60 mmol) and the reaction mixture was stirred for 48 h. The reaction was evaporated to dryness under a stream of N2 and the crude product redissolved in acetonitrile (1.0 mL). 1-Boc-piperazine (22.3 mg, 0.12 mmol) was added and the reaction mixture was refluxed for 4 h. The reaction mixture was concentrated under reduced pressure, redissolved in CH2Cl2 and passed through a short pad of SiO2, providing the 1-Boc-4-diphenylmethylpiperazine. The reaction was evaporated to dryness under a stream of N2 the crude product redissolved in acetonitrile (1.0 mL) the reaction mixture was refluxed for 4 h The reaction mixture was concentrated under reduced pressure redissolved in CH2Cl2

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

Procedure: This material was prepared from 4,4′-dibromobenzhydrol (84) using the procedure described for compound (8) (6.15 g, 66%).

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

Procedure: This material was prepared from 4,4′-dibromobenzophenone using the procedure described for compound (7) (9.67 g, 96%).

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

Procedure: A solution of bis-(4-bromophenyl)methanone (406 mg, 1.19 mmol) in THF (12 mL) is cooled to 0° C., treated portion-wise with sodium borohydride (37.8 mg, 0.893 mmol), and stirred at RT overnight. The reaction mixture is again cooled to 0° C., then quenched with 1 N HCl. Water is added, and the mixture is extracted with ethyl acetate (3×). The combined organic layers are dried and concentrated to give bis-(4-bromophenyl)methanol (410 mg, in excess of theoretical yield) as a crude residue to be used as is. The reaction mixture is again cooled to 0° C. quenched with 1 N HCl Water is added the mixture is extracted with ethyl acetate (3×) The combined organic layers are dried concentrated