Tools · Synthesis

Reaction Scale Calculator

Pick a stored reaction, fix one reagent's amount, get every other reagent's quantity by stoichiometric equivalents. Solvent volume derived from your substrate concentration. Densities + molar masses come from our molecule database.

Switch reaction

Press / to jump here from anywhere. Type to search all 3374 reactions.

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

Ar–Br + Ar'–B(OH)₂ → Ar–Ar' (Pd(0), base)

Canonical Pd(0)-catalysed cross-coupling of an aryl halide with an aryl boronic acid. The 4-cyanobiphenyl target is the textbook demonstration substrate — electron-poor aryl halide + electron-rich boronic acid, matched polarity for a clean transmetalation. Same pair appears in the ORD-shaped test fixture at tests/fixtures/ord/suzuki_simple.json.

Conditions: Pd(PPh3)4 (5 mol%), K2CO3 (2 equiv, heterogeneous solid base), 1,4-dioxane (or dioxane:H2O 4:1 for hydrolytically robust substrates). Reflux 80–90 °C, 4–24 h. Argon or N2 atmosphere. Workup: cool, partition between EtOAc + brine, wash organic with sat. NaHCO3 + brine, dry MgSO4, concentrate, recrystallise from EtOH or chromatograph (hexane/EtOAc).

Expected yield: 70–85 %
Expected duration: 4–24 h at 80–90 °C (reflux)

Mechanism reference ↗

Anchor reagent — fix this amount, scale everything else Substrate concentration · M

Amount r Unit

Updates as you type · the URL captures every input.

Reactants

Reactants for Suzuki–Miyaura coupling: 4-bromobenzonitrile + phenylboronic acid → 4-cyanobiphenyl: stoichiometric quantities derived from the anchor amount.
Reagent	Equiv	Moles · mmol	Mass · g	Volume · mL
623-00-7 623-00-7 · C7H4BrN density unavailable — volume not calculable.	1.0	10.00	1.820	—
Phenylboronic Acid 98-80-6 · C6H7BO2 density unavailable — volume not calculable.	1.1	11.00	1.341	—

Catalyst

Catalyst for Suzuki–Miyaura coupling: 4-bromobenzonitrile + phenylboronic acid → 4-cyanobiphenyl: stoichiometric quantities derived from the anchor amount.
Reagent	Equiv	Moles · mmol	Mass · g	Volume · mL
Tetrakis(Triphenylphosphine)Palladium 14221-01-3 · C72H60P4Pd density unavailable — volume not calculable.	0.05	0.50	0.578	—

Solvent

Solvent for Suzuki–Miyaura coupling: 4-bromobenzonitrile + phenylboronic acid → 4-cyanobiphenyl: stoichiometric quantities derived from the anchor amount.
Reagent	Equiv	Moles · mmol	Mass · g	Volume · mL
123-91-1 123-91-1 · C4H8O2	—	490.98	43.260	42.00

Product

Product for Suzuki–Miyaura coupling: 4-bromobenzonitrile + phenylboronic acid → 4-cyanobiphenyl: stoichiometric quantities derived from the anchor amount.
Reagent	Equiv	Moles · mmol	Mass · g	Volume · mL
2920-38-9 2920-38-9 · C13H9N	1.0	10.00	1.792	—

Expected isolated yield

What you should actually weigh out of the recrystallisation flask, scaled from the limiting reactant via the canonical-procedure yield window.

Product: 2920-38-9 2920-38-9 · C13H9N
Theoretical max: 1.79 g (10.00 mmol)
Expected isolated · 70–85 % yield: 1.25 – 1.52 g

Stoichiometry: moles_X = (moles_anchor / equiv_anchor) × equiv_X. Mass = moles × MW; volume = mass / ρ. Solvent volume = total reactant moles ÷ substrate concentration.