1-(dimethoxyphosphorylmethyl)-4-fluorobenzene

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: Following the procedure of Compound 11, 4-chloro-1-bromomethylnaphthalene is reacted with trimethylphosphite.

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

Procedure: Following the procedure of Compound 11, 2-chlorobenzyl bromide is reacted with trimethylphosphite.

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

Procedure: Following the procedure of Compound 11, 3-fluorobenzyl bromide is reacted with trimethylphosphite.

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

Procedure: Following the procedure of Compound 11, 2-fluorobenzyl bromide is reacted with trimethylphosphite.

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

Procedure: Following the procedure of Compound 11, 4-methylbenzyl bromide is reacted with trimethylphosphite.

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

Procedure: Following the procedure of Compound 11, 3-methylbenzyl bromide is reacted with trimethylphosphite.

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

Procedure: Following the procedure of Compound 11, 2-methylbenzyl bromide is reacted with trimethylphosphite.

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

Procedure: A mixture of 4-fluorobenzyl bromide (4.86 g, 0.026M) and trimethylphosphite (10 mL, 0.085M) is heated at the reflux temperature for 48 hours. The solution is cooled and excess trimethylphosphite is removed under reduced pressure. The crude product is chromatographed over silica gel (40-63 mμ, 400 g, 45 mL fractions, ethyl acetate), eluting with ethyl acetate. Fractions 41-80 are combined, concentrated, and placed under vacuum for 36 hours. The product (4.52 g) is a colorless oil. is heated at the reflux temperature for 48 hours The solution is cooled excess trimethylphosphite is removed under reduced pressure The crude product is chromatographed over silica gel (40-63 mμ, 400 g, 45 mL fractions, ethyl acetate) eluting with ethyl acetate concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bromotrimethylsilane (6.0 mL, 45.4 mmol) was added dropwise to (4-fluoro-benzyl)-phosphonic acid dimethyl ester (4.57 g, 20.95 mmol) and stirred in a reaction flask chilled to 0° C. The resulting solution was allowed to warm to ambient temperature and stirred for an additional hour, then concentrated by rotary evaporation to remove volatiles yielding crude (4-fluoro-benzyl) phosphonic acid bis(trimethylsilyl) ester which was used without further purification. to warm to ambient temperature stirred for an additional hour concentrated by rotary evaporation to remove volatiles