Dichloromethane → HCID 86633519, compound

HRID 2428068Notes

Reaction equation

HRID 2428068 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)[CH:20]=[C:19]([Br:24])[N:18]=1.ClCCl.C(N(CC)CC)C>O.CN1CCCC1=O>[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

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 134959192,4,6-TribromopyridineHCID 16641178Ethyl (4-mercapto-2-methylphenoxy)acetate

Product 1

HCID 86633519HCID 86633519, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

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 mmol; prepared as described in Chem. Ber. 1989, 122, 489), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium complex with dichloromethane (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-(2,6-dibromopyridine-4-ylsulfanyl)-2-methylphenoxy]acetate.

Workup

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

Sources & evidence

ORD record
ord-5d2dc70cbd2c457d94c263d1d4c39368
Source dataset
uspto-grants-2011_06
Patent number
US07968723B2

Reaction notes

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