1,3-difluoro-5-pentylbenzene

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

Procedure: A solution of n-butyllithium (10.4M in hexane; 2.70 ml, 0.028 mol) was added dropwise to a stirred, cooled (-78° C.) solution of compound 13 (5.00 g, 0.027 mol) in dry THF (60 ml) under dry nitrogen. The stirred mixture was maintained under these conditions for 2.5 h and a previously cooled solution of tri-isopropyl borate (10.22 g, 0.054 mol) in dry THF (50 ml) was added dropwise at -78° C. The stirred mixture was allowed to warm to room temperature overnight and stirred for 1 h with 10% hydrochloric acid (30 ml). The product was extracted into ether (twice), and the combined ethereal extracts were washed with water and dried (MgSO4). The solvent was removed in vacuo to give a colourless solid. The stirred mixture was maintained under these conditions for 2.5 h The product was extracted into ether (twice), and the combined ethereal extracts were washed with water dried (MgSO4) The solvent was removed in vacuo to give a colourless solid

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

Procedure: A solution of n-butyllithium (10.5M in hexane; 2.70 ml, 0.028 mol) was added dropwise to a stirred, cooled (-78° C.) solution of compound 13 (5.10 g, 0.028 mol) in dry THF (30 ml) under dry nitrogen. The stirred mixture was maintained under these conditions for 2.5 h and then poured onto a slurry of solid carbon dioxide and dry ether. The product was extracted into 10% sodium hydroxide which was then acidified with 36% hydrochloric acid. The acidic mixture was washed with ether (twice), and the combined ethereal layers were washed with water and dried (MgSO4). The solvent was removed in vacuo to yield a colourless solid. The stirred mixture was maintained under these conditions for 2.5 h The product was extracted into 10% sodium hydroxide which The acidic mixture was washed with ether (twice), and the combined ethereal layers were washed with water dried (MgSO4) The solvent was removed in vacuo to yield a colourless solid

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

Procedure: A solution of n-butyllithium (10.5M in hexane; 2.70 ml, 0.028 mol) was added dropwise to a stirred, cooled (-78° C.) solution of compound 13 (5.10 g, 0.028 mol) in dry THF (30 ml) under dry nitrogen. The stirred mixture was maintained under these conditions for 2.5 h and then poured onto a slurry of solid carbon dioxide and dry ether. The product was extracted into 10% sodium hydroxide which was then acidified with 36% hydrochloric acid. The acidic mixture was washed with ether (twice), and the combined ethereal layers were washed with water and dried (MgSO4). The solvent was removed in vacuo to yield a colourless solid. The stirred mixture was maintained under these conditions for 2.5 h The product was extracted into 10% sodium hydroxide which The acidic mixture was washed with ether (twice), and the combined ethereal layers were washed with water dried (MgSO4) The solvent was removed in vacuo to yield a colourless solid

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

Procedure: A solution of n-butyllithium (10.4M in hexane; 2.70 ml, 0.028 mol) was added dropwise to a stirred, cooled (-78° C.) solution of compound 13 (5.00 g, 0.027 mol) in dry THF (60 ml) under dry nitrogen. The stirred mixture was maintained under these conditions for 2.5 h and a previously cooled solution of tri-isopropyl borate (10.22 g, 0.054 mol) in dry THF (50 ml) was added dropwise at -78° C. The stirred mixture was allowed to warm to room temperature overnight and stirred for 1 h with 10% hydrochloric acid (30 ml). The product was extracted into ether (twice), and the combined ethereal extracts were washed with water and dried (MgSO4). The solvent was removed in vacuo to give a colourless solid. The stirred mixture was maintained under these conditions for 2.5 h The product was extracted into ether (twice), and the combined ethereal extracts were washed with water dried (MgSO4) The solvent was removed in vacuo to give a colourless solid

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

Procedure: A solution of n-butyllithium (10.5M in hexane; 2.70 ml, 0.028 mol) was added dropwise to a stirred, cooled (-78° C.) solution of compound 13 (5.10 g, 0.028 mol) in dry THF (30 ml) under dry nitrogen. The stirred mixture was maintained under these conditions for 2.5 h and then poured onto a slurry of solid carbon dioxide and dry ether. The product was extracted into 10% sodium hydroxide which was then acidified with 36% hydrochloric acid. The acidic mixture was washed with ether (twice), and the combined ethereal layers were washed with water and dried (MgSO4). The solvent was removed in vacuo to yield a colourless solid. The stirred mixture was maintained under these conditions for 2.5 h The product was extracted into 10% sodium hydroxide which The acidic mixture was washed with ether (twice), and the combined ethereal layers were washed with water dried (MgSO4) The solvent was removed in vacuo to yield a colourless solid