Sodium Carbonate → 2-(3-thienyl)benzaldehyde

HRID 1836672Notes

Reaction equation

HRID 1836672 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[S:10]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11]1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:10]1[CH:14]=[CH:13][C:12]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:11]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 811292-BromobenzaldehydeHCID 581760Thiophene-3-boronic acid

Product 1

HCID 43213152-(3-thienyl)benzaldehyde

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

The reaction was repeated on a 50 mmol scale with 2-bromobenzaldehyde (5.8 mL), thiophene-3-boronic acid (7.03 g, 0.0555 mol) in ethanol (55 mL), Pd(PPh3)4 (1.7 g, 3 mol %), 2 M aqueous Na2CO3 (55 mL) in toluene (275 mL) to yield crude 2-(3-thienyl)benzaldehyde as an oil.

Sources & evidence

ORD record
ord-7778c2f78bb843feabed8eb6452c5c2a
Source dataset
uspto-grants-2004_08
Patent number
US06777421B2

Reaction notes

Loading…