4-bromo-2-chloro-1-propan-2-yloxybenzene

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

Procedure: The intermediate bromide, was prepared analogously to Step 1 in Example A(52), where 4-Bromo-2-chloro-phenol was substituted in place of 4-bromo-2-fluorophenol and 2-iodopropane instead of methyl □-bromobutyrate of that example.

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

Procedure: The ketone intermediate, was prepared analogously to Example A(27), where 4-Bromo-2-chloro-1-isopropoxy-benzene (from Step 3 below) was substituted in place of 3-Cyclohex-1-enyl-1-cyclopentyl-propan-1-one in Step 1 of that example.

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

Procedure: The ketone intermediate, was prepared analogously to Example A(27), where 4-Bromo-2-chloro-1-isopropoxy-benzene (from Step 3 below) was substituted in place of 3-Cyclohex-1-enyl-1-cyclopentyl-propan-1-one in Step 1 of that example.

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromo-2-chlorophenol (50 g) in N,N-dimethylformamide (DMF) (250 mL) stirred under nitrogen at room temperature was added K2CO3 (100 g) and 2-bromopropane (136 mL) in one charge. The reaction mixture was stirred at 85° C. for 16 h. After cooling the reaction, the reaction mixture was filtered, the solvent of the filtrate was removed in vacuo. The residue was dissolved in diethyl ether (300 mL), washed with water (6*100 mL), the organic phase was dried over MgSO4 and concentrated to give 4-bromo-2-chlorophenyl 1-methylethyl ether (D68) (56 g) as a yellow oil. δH (CDCl3, 400 MHz): 1.37 (6H, d), 4.52 (1H, m), 6.82 (1H, d), 7.29 (1H, m), 7.50 (1H, d). charge After cooling the reaction the reaction mixture was filtered the solvent of the filtrate was removed in vacuo The residue was dissolved in diethyl ether (300 mL) washed with water (6*100 mL) the organic phase was dried over MgSO4 concentrated

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

Procedure: The intermediate bromide, was prepared analogously to Step 1 in Example A(52), where 4-Bromo-2-chloro-phenol was substituted in place of 4-bromo-2-fluorophenol and 2-iodopropane instead of methyl □-bromobutyrate of that example.

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

Procedure: The ketone intermediate, was prepared analogously to Example A(27), where 4-Bromo-2-chloro-1-isopropoxy-benzene (from Step 3 below) was substituted in place of 3-Cyclohex-1-enyl-1-cyclopentyl-propan-1-one in Step 1 of that example.

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

Procedure: The intermediate bromide, was prepared analogously to Step 1 in Example A(52), where 4-Bromo-2-chloro-phenol was substituted in place of 4-bromo-2-fluorophenol and 2-iodopropane instead of methyl □-bromobutyrate of that example.

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

Procedure: The ketone intermediate, was prepared analogously to Example A(27), where 4-Bromo-2-chloro-1-isopropoxy-benzene (from Step 3 below) was substituted in place of 3-Cyclohex-1-enyl-1-cyclopentyl-propan-1-one in Step 1 of that example.