5-bromo-1,3-difluoro-2-iodobenzene

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

Procedure: First, 50 ml of ethanol containing 5.61 g of 4-(trans-4-pentylcyclohexyl)phenylboronic acid dissolved therein, 50 ml of benzene containing 5.0 g of 4-bromo-2,6-difluoro-1-iodobenzene dissolved therein, 15.7 ml of a sodium carbonate aqueous solution with a concentration of 2.0 mol/l, and 0.45 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 200 ml flask, and stirred under reflux for 48 hours. After the reaction, water and ether were added to the reaction solution for extraction. The resultant ether layer was washed with a saturated brine and dried with sodium sulfate. The solvent was then distilled off. The residue was purified by silica gel column chromatography (eluent:hexane) and recrystallized from acetone, to obtain 2.58 g (Y: 39.1%) of 4-bromo-2,6-difluoro-4′-(trans-4-pentylcyclohexyl)biphenyl. The purity of the resultant compound was 100.0% as measured by GC. (5-b) Synthesis of polymerizable compound 2,6-difluoro-4′-(trans-4-pentylcyclohexyl)-4-vinylbiphenyl represented by formula (E) above under reflux for 48 hours were added to the reaction solution for extraction The resultant ether layer was washed with a saturated brine dried with sodium sulfate The solvent was then distilled off The residue was purified by silica gel column chromatography (eluent:hexane) recrystallized from acetone

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

Procedure: The title compound is prepared from 5-bromo-1,3-difluoro-2-iodo-benzene and 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-triisopropylsilanyl-oxazole following a procedure analogous to that described in Intermediate 27. LC (method 1): tR=1.18 min; Mass spectrum (ESI+): m/z=260 [M+H]+.