4-Bromobenzaldehyde → 4-Cyclopropylbenzaldehyde

HRID 1615049Notes

Reaction equation

HRID 1615049 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F-].[K+].[CH:12]1(B(O)O)[CH2:14][CH2:13]1>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:12]1([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 707414-BromobenzaldehydeHCID 522689Potassium FluorideHCID 2760897Cyclopropylboronic acid

Product 1

HCID 115064744-Cyclopropylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-bromobenzaldehyde (94 g) in toluene (470 mL) were added potassium fluoride (95 g), cyclo-propylboronic acid (48 g) and bis(triphenylphosphine)-palladium (II) dichloride (3.6 g) under nitrogen atmosphere. The reaction mixture was stirred at 110° C. for 24 hr under nitrogen atmosphere. The reaction mixture was filtered using Celite. The filtrate was concentrated in vacuo to give the crude title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a9d6cd9c69b344318c3d1711033f21af
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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