Dichloromethane → Ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-propylbenzoate

HRID 2177707Notes

Reaction equation

[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.[Br-].[CH2:29]([Zn+])[CH2:30][CH3:31]>C1COCC1.[Cu]I>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14]([CH2:29][CH2:30][CH3:31])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 61, 0.1 g), palladium chloride dppf adduct with DCM (0.01 g), copper (I) iodide (0.003 g) and n-propyl zinc bromide (0.5M solution in THF, 0.96 ml) in THF (0.5 ml) was stirred and heated in the microwave at 160° C. for 10 minutes. After cooling, the mixture was filtered and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60% to give ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-propylbenzoate (0.034 g) as a clear gum.

Workup

temperatureAfter cooling
filtrationthe mixture was filtered
customthe filtrate was evaporated to dryness
customThe residue was purified by chromatography on silica
washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60%

Sources & evidence

ORD record: ord-24d4d4a16b2f4bfe944492ac59029737
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067905B2

Reaction notes

Loading…