Dimethylformamide → Benzoyl chloride

HRID 650023Notes

Reaction equation

HRID 650023 reaction equation
Cl.N1(CCOC2C=CC(C(O)=O)=CC=2)CCCC1.Cl.[C:20]([Cl:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.S(Cl)(Cl)=O.CN(C=O)C>ClCCl>[C:20]([Cl:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 131748684-(2-Pyrrolidin-1-ylethoxy)benzoic acid hydrochlorideHCID 22344169HCID 22344169, compound

Product 1

HCID 7412Benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By converting 4-[2-(1-pyrrolidinyl)ethoxy]benzoic acid hydrochloride into the corresponding benzoyl chloride hydrochloride using thionyl chloride and catalytic DMF in refluxing dichloromethane to form the benzoyl choride, followed by acylation using AlCl3 in 1,2-dichloroethane at 0° C., the title compound was prepared from 2-(4-methoxyphenyl)benzo[b]thiophene in 59% yield as an oil following radial chromatography (SiO2; gradient of 2-5% MeOH in CH2Cl2).

Sources & evidence

ORD record
ord-757d05879d5f4e1a8d6796239d975221
Source dataset
uspto-grants-2001_08
Patent number
US06271227B1

Reaction notes

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