2-(3-bromophenoxy)-N,N-dimethylethanamine

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: 3-Bromophenol (0.870 g, 5.00 mmol), (2-chloro-ethyl)-dimethylamine hydrochloride (0.792 g, 5.50 mmol) and Cs2CO3 (8 g, 25 mmol) were combined in DMF (20 mL) and the mixture was heated at reflux over night. H2O (20 mL) was added and the mixture was extracted with EtOAc, then washed with 2N NaOH and brine. The organic layers were combined, dried over Na2SO and concentrated to a brown oil which was then purified by flash chromatography (eluent: 20% EtOAc in hexanes). the mixture was heated at reflux over night the mixture was extracted with EtOAc washed with 2N NaOH and brine dried over Na2SO concentrated to a brown oil which was then purified by flash chromatography (eluent: 20% EtOAc in hexanes)

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

Procedure: 3-Bromophenol (0.870 g, 5.00 mmol), (2-chloro-ethyl)-dimethylamine hydrochloride (0.792 g, 5.50 mmol) and Cs2CO3 (8 g, 25 mmol) were combined in DMF (20 mL) and the mixture was heated at reflux over night. H2O (20 mL) was added and the mixture was extracted with EtOAc, then washed with 2N NaOH and brine. The organic layers were combined, dried over Na2SO and concentrated to a brown oil which was then purified by flash chromatography (eluent: 20% EtOAc in hexanes). the mixture was heated at reflux over night the mixture was extracted with EtOAc washed with 2N NaOH and brine dried over Na2SO concentrated to a brown oil which was then purified by flash chromatography (eluent: 20% EtOAc in hexanes)

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

Procedure: Prepared from [2-(3-bromo-phenoxy)-ethyl]-dimethyl-amine according to general Method I for borylation described above for preparation of 4,4,5,5-tetramethyl-2-(2-methyl-4-phenoxy-phenyl)-[1,3,2]dioxaborolane.

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: Diisopropyl diazene-1,2-dicarboxylate (1.1 eq.) was added dropwise to a 0° C. solution of 3-bromophenol (1.155 g, 6.68 mmol, 1.0 eq.), 2-(dimethylamino)ethanol (1.1 eq.) and triphenylphosphine (1.1 eq.) in THF (20 mL). The mixture was allowed to warm to room temperature over 16 hours, and then the volatiles were removed under reduced pressure. The resulting residue was partitioned between EtOAc (20 mL) and 1N HCl (20 mL), and the aqueous layer was collected and washed with EtOAc. The aqueous layer was neutralized with saturated NaHCO3 (50 mL), extracted with EtOAc, and dried (MgSO4). Purification via silica chromatography (eluting with 4% MeOH/DCM) afforded 2-(3-bromophenoxy)-N,N-dimethylethanamine (1.032 g, 63%) as an oil. the volatiles were removed under reduced pressure The resulting residue was partitioned between EtOAc (20 mL) and 1N HCl (20 mL) the aqueous layer was collected washed with EtOAc extracted with EtOAc dried (MgSO4) Purification via silica chromatography (eluting with 4% MeOH/DCM)

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

Procedure: Diisopropyl diazene-1,2-dicarboxylate (1.56 g, 7.34 mmol) was added dropwise to a 0° C. solution of 3-bromophenol (1.155 g, 6.68 mmol), 2-(dimethylamino)ethanol (0.65 g, 7.34 mmol) and triphenylphosphine (1.93 g, 7.34 mmol) in THF (20 mL). The mixture was allowed to warm to room temperature over 16 hours, and then the volatiles were removed under reduced pressure. The resulting residue was partitioned between ethyl acetate (20 mL) and 1N HCl (20 mL), and the aqueous layer was collected and washed with ethyl acetate. The aqueous layer was neutralized with saturated NaHCO3 (50 mL), extracted with ethyl acetate, and dried (MgSO4). Purification via silica chromatography (eluting with 4% MeOH/DCM) afforded 2-(3-bromophenoxy)-N,N-dimethylethanamine (1.03 g, 63%) as an oil. the volatiles were removed under reduced pressure The resulting residue was partitioned between ethyl acetate (20 mL) and 1N HCl (20 mL) the aqueous layer was collected washed with ethyl acetate extracted with ethyl acetate dried (MgSO4) Purification via silica chromatography (eluting with 4% MeOH/DCM)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Bromophenol (1 eq, 1.156 mmol, 0.2 g), 2-chloro-N,N-dimethylethanamine (1.1 eq, 1.272 mmol, 0.137 g) and potassium carbonate (3 eq, 3.47 mmol, 0.479 g) are mixed together in NMP (5 ml). The reaction mixture is heated at 80° C. for 6 hrs. The reaction mixture is dissolved in EtOAC and washed with water. The organic layer is washed with brine, dried over drying agent MgSO4, filtered and the organic solvent is reduced in vacuo to afford [2-(3-Bromo-phenoxy)-ethyl]-dimethyl-amine; [M+H]+ 245/247 The reaction mixture is dissolved in EtOAC washed with water The organic layer is washed with brine dried over drying agent MgSO4 filtered

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

Procedure: N,N-Dimethyl-2-(3-bromophenoxy)ethylamine (2.87 g, 11.7 mmol) and ethyl trifluoroacetate (2.5 g, 17.6 mmol) were reacted by the general procedure as described in the preparation of [4-[2-(N,N-dimethylamino)ethoxy]phenyl]-2,2,2-trifluoroethanone. The residue was distilled under reduced pressure to afford the title compound (1.34 g, 44%) as a pale yellow liquid. Analytically pure sample was obtained by a second distillation under reduced pressure. Analysis for C12H14F3NO2.0.8H2O calcd. C 52.29%, H 5.70%, N 5.08%; Found: C 52.61%, H 5.53%, N 4.96%. The residue was distilled under reduced pressure

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

Procedure: 3-Bromophenol (5.0 g, 28.9 mmol) and 2-(N,N-dimethylamino)ethyl chloride, hydrochloride (6.24 g, 43.3 mmol) were reacted by the general procedures as described in the preparation of N,N-dimethyl-2-(4-bromophenoxy)ethylamine. The residue was chromatographed on silica gel (dichloromethane/methanol 100:0 to 90:10) to give the title compound (5.2 g, 74%) as a pale yellow liquid. The residue was chromatographed on silica gel (dichloromethane/methanol 100:0 to 90:10)