2-bromo-3-fluorophenol

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

Procedure: A mixture of commercially available 2-bromo-3-fluorophenol (5.000 g; 26.20 mmol), iodoethane (8.166 g; 52.40 mmol), and K2CO3 (4.342 g; 31.40 mmol) in anh. DMF (100 ml) was heated to 80° C., under nitrogen, for 1.5 h. Et2O was added and the organic layer was washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 2-bromo-1-ethoxy-3-fluorobenzene as a yellow oil. LC-MS (conditions A): tR=0.88 min.; no ionisation. the organic layer was washed with water dried over anh. MgSO4 filtered concentrated to dryness under reduced pressure

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Bromo-3-fluoro anisole (10 g, 48.77 mmol) was dissolved in DCM (200 mL) and cooled to about −78° C. To the solution was added BBr3 (11.53 mL, 121.9 mmol) in one portion. The mixture was warmed to r.t. and stirred overnight. The mixture was partitioned between water and DCM (50 mL), and the aqueous layer was back extracted with DCM (200 mL). The combined organics were dried (NaSO4), filtered and concentrated to give about 9.32 g of the product as a dark oil. MS found 188.9 (M−1) The mixture was warmed to r.t. The mixture was partitioned between water and DCM (50 mL) the aqueous layer was back extracted with DCM (200 mL) The combined organics were dried (NaSO4) filtered concentrated

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

Procedure: A mixture of commercially available 2-bromo-3-fluorophenol (5.000 g; 26.20 mmol), iodoethane (8.166 g; 52.40 mmol), and K2CO3 (4.342 g; 31.40 mmol) in anh. DMF (100 ml) was heated to 80° C., under nitrogen, for 1.5 h. Et2O was added and the organic layer was washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 2-bromo-1-ethoxy-3-fluorobenzene as a yellow oil. LC-MS (conditions A): tR=0.88 min.; no ionisation. the organic layer was washed with water dried over anh. MgSO4 filtered concentrated to dryness under reduced pressure

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Bromo-3-fluoro anisole (10 g, 48.77 mmol) was dissolved in DCM (200 mL) and cooled to about −78° C. To the solution was added BBr3 (11.53 mL, 121.9 mmol) in one portion. The mixture was warmed to r.t. and stirred overnight. The mixture was partitioned between water and DCM (50 mL), and the aqueous layer was back extracted with DCM (200 mL). The combined organics were dried (NaSO4), filtered and concentrated to give about 9.32 g of the product as a dark oil. MS found 188.9 (M−1) The mixture was warmed to r.t. The mixture was partitioned between water and DCM (50 mL) the aqueous layer was back extracted with DCM (200 mL) The combined organics were dried (NaSO4) filtered concentrated