Triethylamine → HCID 86633519, compound

HRID 2428077Notes

Reaction equation

[SH:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([CH3:15])[CH:3]=1.[Br:16][C:17]1[CH:22]=[C:21]([Br:23])[CH:20]=[C:19]([Br:24])[N:18]=1.C(N(CC)CC)C.CN1CCCC1=O>O>[Br:23][C:21]1[CH:22]=[C:17]([Br:16])[N:18]=[C:19]([S:1][C:2]2[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([CH3:15])[CH:3]=2)[CH:20]=1.[Br:16][C:17]1[CH:22]=[C:21]([S:1][C:2]2[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([CH3:15])[CH:3]=2)[CH:20]=[C:19]([Br:24])[N:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of ethyl (4-mercapto-2-methylphenoxy)acetate (1.0 g, 4.4 mmol), 2,4,6-tribromopyridine (1.26 g, 4.0 mmol; prepared as described in Chem. Ber. 1989, 122, 489), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (0.163 g, 0.20 mmol), triethylamine (1.23 mL, 8.8 mmol) and N-methylpyrrolidinone (12 mL) was heated under nitrogen at 80° C. for 3 h. The reaction mixture was then poured into water (60 mL) and extracted with ethyl acetate (3×70 mL). The combined organic layers were dried with anhydrous magnesium sulfate and evaporated in vacuo. Column chromatography of the crude product (silica gel Fluka 60, hexanes/ethyl acetate 98:2-80:20) afforded ethyl [4-(4,6-dibromopyridin-2-ylsulfanyl)-2-methylphenoxy]acetate as the minor product and ethyl [4-(2,6-dibromopyridin-4-ylsulfanyl)-2-methylphenoxy]acetate as the major product.

Workup

extractionextracted with ethyl acetate (3×70 mL)
dry with materialThe combined organic layers were dried with anhydrous magnesium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-08654e0078dc4135b28df26b7287d7a9
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968723B2

Reaction notes

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