chempirical

Suzuki–Miyaura coupling: 4-bromobenzonitrile + phenylboronic acid → 4-cyanobiphenyl

Reagent table at any scale. Enter how much 4-bromobenzonitrile you have, or pick another reagent, and every mass, volume and amount follows.

Conditions and workup
NBr4-Bromobenzonitrile+HOBHOPhenylboronic acidK2CO3 (2.0 equiv)Pd(PPh3)4 (5 mol%)1,4-dioxaneN(1,1'-Biphenyl)-4-carbonitrile70–85 %
NBr4-Bromobenzonitrile+HOBHOPhenylboronic acidK2CO3 (2.0 equiv)Pd(PPh3)4 (5 mol%)1,4-dioxaneN(1,1'-Biphenyl)-4-carbonitrile70–85 %

Reagent table

ReagentRoleEquivMW (g/mol)ρ (g/mL)nmV
4-Bromobenzonitrile623-00-7limitingyour amount reactant 182.02 — 5.49 mmol 1.00e+3 mg —
Phenylboronic acid98-80-6 reactant 121.93 — 6.04 mmol 737 mg —
Potassium carbonate584-08-7 reagent 138.21 — 11.0 mmol 1.52 g —
Tetrakis(triphenylphosphine)palladium14221-01-3 catalyst5 mol% 1155.59 — 0.275 mmol 317 mg —
1,4-Dioxane123-91-1 solvent — 88.11 1.030 — — 11.0 mL
(1,1'-Biphenyl)-4-carbonitrile2920-38-9 product — 179.22 — 5.49 mmol 985 mg —
Theoretical yield985 mg5.49 mmol of (1,1'-biphenyl)-4-carbonitrile
Expected at 70–85 %689 mg – 837 mgtypical isolated yield
Solvent11.0 mL1,4-Dioxane, 0.5 M
Limiting reagent4-Bromobenzonitrile
Notes on the reagents
4-Bromobenzonitrile
4-Bromobenzonitrile — electron-poor aryl halide; coupling partner.
Phenylboronic acid
Phenylboronic acid — electron-rich aryl boronic acid; slight excess to compensate for protodeboronation.
Tetrakis(triphenylphosphine)palladium
Tetrakis(triphenylphosphine)palladium(0) — 5 mol%. Air-stable enough for bench setup but degas anyway.
1,4-Dioxane
1,4-Dioxane — primary solvent. Often used as 4:1 dioxane/H2O for boronic-acid solubility; the calculator does not split solvent volumes, so adjust by hand if you want the aqueous mix.
(1,1'-Biphenyl)-4-carbonitrile
4-Cyanobiphenyl — pale-yellow crystalline; mp 86–88 °C; recrystallises from EtOH.
How the amounts are calculated

The amount you enter is converted to millimoles with the molar mass, or with density and molar mass for a volume. Dividing by its equivalents gives the millimoles per equivalent; every other reagent is that times its own equivalents. Masses use the molar mass of the structure. Volumes are given for compounds that are liquid at room temperature and have a density on file. A reagent sold as a solution, such as n-BuLi in hexanes, gets the volume of that solution; enter your bottle's titre and every volume follows.

The theoretical yield assumes full conversion of the limiting reagent: the reactant with the fewest millimoles per stoichiometric coefficient. Change an equivalent and the limiting reagent may change with it.

Solvent volume and concentration

The concentration refers to the substrate, the limiting reagent: solvent volume = millimoles of substrate ÷ concentration, since 1 M is 1 mmol/mL. Liquid reagents add to the final volume, so the real concentration ends up slightly lower. Leave the field empty to leave the solvent out.

What the table cannot know

Purity, water content and reagents sold as solutions. Grignard reagents and organolithiums are bought as solutions: take the millimoles from the table and divide by the molarity on the bottle to get the volume to syringe out.

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