6-bromo-1,1,1-trifluorohexane

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

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

Procedure: Commercially available 6-bromo-1,1,1-trifluorohexane (Oakwood) and trimethylamine oxide were processed using the method described in example 137A to afford the title compound. MS (ESI+) m/z 154 (M+NH4—H2O)+.

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

Procedure: Commercially available 6-bromo-1,1,1-trifluorohexane (Oakwood) and trimethylamine oxide were processed using the method described in example 137A to afford the title compound. MS (ESI+) m/z 154 (M+NH4—H2O)+.

Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of thiophene (4.2 g) in dry tetrahydrofuran (25 ml) at -15° C. under nitrogen, was added n-butyllithium (20 ml, 2.5M) dropwise and the solution stirred at -15° C. for 2 hours. The solution was then cooled to -78° C. and 6,6,6-trifluorohexylbromide (10.95 g) in dry tetrahydrofuran (20 ml) was added and solution stirred at -78° C. for 1 hour, allowed to warm to room temperature and stirred overnight. The reaction mixture was poured onto ice, extracted with ether (2×75 ml), dried over MgSO4 and evaporated under reduced pressure to give a brown oil. The oil was distilled under reduced pressure to give a colourless oil, b.p. 66° C./20 mm. The solution was then cooled to -78° C. solution stirred at -78° C. for 1 hour to warm to room temperature stirred overnight The reaction mixture was poured onto ice extracted with ether (2×75 ml) dried over MgSO4 evaporated under reduced pressure to give a brown oil The oil was distilled under reduced pressure to give a colourless oil, b.p. 66° C./20 mm

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

Procedure: Commercially available 6-bromo-1,1,1-trifluorohexane (Oakwood) and trimethylamine oxide were processed using the method described in example 137A to afford the title compound. MS (ESI+) m/z 154 (M+NH4—H2O)+.

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

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

Procedure: Commercially available 6-bromo-1,1,1-trifluorohexane (Oakwood) and trimethylamine oxide were processed using the method described in example 137A to afford the title compound. MS (ESI+) m/z 154 (M+NH4—H2O)+.

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

Procedure: Commercially available 6-bromo-1,1,1-trifluorohexane (Oakwood) and trimethylamine oxide were processed using the method described in example 137A to afford the title compound. MS (ESI+) m/z 154 (M+NH4—H2O)+.

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

Procedure: To a suspension of 4-hydroxybenzaldehyde (488 mg, 4 mmol) and 6-bromo-1,1,1-trifluorohexane (657 mg, 3 mmol) in MeCN (10 mL) was added K2CO3 (829 mg, 6.00 mmol). The resulting mixture was reflux overnight. Insoluble material was filtered off and rinsed with MeCN. The combined filtrate was concentrated to afford a white solid. This white solid was partitioned between EtOAc and 1 N NaOH solution. The organic layer was separated, washed with sat'd NH4Cl, dried over MgSO4, filtered and concentrated to afford Intermediate 8A as a clear liquid. LCMS Anal. Calc'd for C13H15F3O2 260.10, found [M+H] 261.0. The resulting mixture was reflux overnight Insoluble material was filtered off rinsed with MeCN The combined filtrate was concentrated to afford a white solid This white solid was partitioned between EtOAc and 1 N NaOH solution The organic layer was separated washed with sat'd NH4Cl dried over MgSO4 filtered concentrated

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-hydroxy-6-chloroacridone (594 mg) was stirred in 10 ml of methanol, and 5 ml of methanolic KOH (30 mg/ml) was added (1 equiv. base), whereupon complete dissolution occurred. 1-Bromo-5-trifluoromethylpentane (2.03 g, 3 equiv.) was added and the solution heated at 70° C. overnight, forming a fine solid precipitate; after cooling, 0.35 g of pale yellow powder was collected by filtration. When the filtrate is heated another 2 days, the same quantity of product may be isolated in addition. The crude product was crystallized from methanol. Analogous procedures can be applied for preparation of compounds with the O(CH2)3CF3, O(CH2)4CF3, O(CH2)7CF3, and O(CH2)10CF3— side chains and including aromatic ketone derivatives bearing O(CH2)C2F5 and O(CH2)C3F7 side chains. whereupon complete dissolution forming a fine solid precipitate after cooling 0.35 g of pale yellow powder was collected by filtration When the filtrate is heated another 2 days the same quantity of product may be isolated in addition The crude product was crystallized from methanol Analogous procedures can be applied for preparation of compounds with the O(CH2)3CF3, O(CH2)4CF3, O(CH2)7CF3, and O(CH2)10CF3— side chains

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

Procedure: To 3,6-dihydroxy-xanthone (0.58 g, 1 equivalent) is added 10 ml of ethanol, then 117 mg of KOH 0.8 equivalents), followed by 0.58 g of CF3(CH2)5Br (1 equivalent); after two hours of boiling this mixture, the pH had dropped to the acidic range, and another 100 mg of KOH was added and heating continued overnight. The cooled mixture was diluted with water (50 ml) and extracted with ethyl acetate (3×50 ml), the combined extracts washed with 5 ml of water and brought to dryness. Separation of the 3-component mixture was achieved by chromatography (100 g of silica gel, column diameter 5 cm) with solvents of increasing polarity: Solvents used: ethyl acetate (A), hexane (isomeric mixture) (B), ethanol (C) the pH had dropped to the acidic range heating continued overnight extracted with ethyl acetate (3×50 ml) the combined extracts washed with 5 ml of water Separation of the 3-component mixture of increasing polarity

Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of thiophene (4.2 g) in dry tetrahydrofuran (25 ml) at -15° C. under nitrogen, was added n-butyllithium (20 ml, 2.5M) dropwise and the solution stirred at -15° C. for 2 hours. The solution was then cooled to -78° C. and 6,6,6-trifluorohexylbromide (10.95 g) in dry tetrahydrofuran (20 ml) was added and solution stirred at -78° C. for 1 hour, allowed to warm to room temperature and stirred overnight. The reaction mixture was poured onto ice, extracted with ether (2×75 ml), dried over MgSO4 and evaporated under reduced pressure to give a brown oil. The oil was distilled under reduced pressure to give a colourless oil, b.p. 66° C./20 mm. The solution was then cooled to -78° C. solution stirred at -78° C. for 1 hour to warm to room temperature stirred overnight The reaction mixture was poured onto ice extracted with ether (2×75 ml) dried over MgSO4 evaporated under reduced pressure to give a brown oil The oil was distilled under reduced pressure to give a colourless oil, b.p. 66° C./20 mm