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

HRID 1466770Notes

Reaction equation

HRID 1466770 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8][CH2:9][C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:20][OH:21].CN([CH:25]=[O:26])C>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:20][O:21][C:25](=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH2:9][C:10](=[O:12])[CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21901440N,N-dimethylformamide methanolHCID 628049741-((3-Bromophenyl)thio)-2-propanone

Product 1

HCID 667650343-(2-Oxo-propylsulfanyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
80 °C

Procedure

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.

Workup

  1. customN2 (g) was bubbled through the solution for 5 minutes
  2. customCO (g) was bubbled into the reaction mixture for five minutes
  3. filtrationThe reaction was worked up then filtered through a plug of silica gel (1:1 EtOAc:hexanes)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6d710b4f8e3843ffbcd1dead602d1ab6
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

Loading…