Triethylamine → 3-(2-Oxo-propylsulfanyl)-benzoic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	N,N-dimethylformamide methanol	HCID 21901440	—
Reactant	1-((3-Bromophenyl)thio)-2-propanone	HCID 62804974	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	3-(2-Oxo-propylsulfanyl)-benzoic acid methyl ester	HCID 66765034	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

1(3-Bromo-phenylsulfanyl)-propan-2-one (4.0 g, 16.3 mmol) was dissolved in MeOH:DMF (1:1, 100 mL) and N2 (g) was bubbled through the solution for 5 minutes. Triethylamine (5.7 mL, 40.8 mmol) and (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.600 g, 0.82 mmol) were added then CO (g) was bubbled into the reaction mixture for five minutes. The reaction was kept under CO atmosphere and heated to 80° C. overnight. The reaction was worked up then filtered through a plug of silica gel (1:1 EtOAc:hexanes) and concentrated to give the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09000025B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-6d710b4f8e3843ffbcd1dead602d1ab6
Source note	uspto-grants-2015_04